diff --git a/core/misc/icons/545560/ex.svg b/core/misc/icons/545560/ex.svg
new file mode 100644
index 0000000000..bef63c1022
--- /dev/null
+++ b/core/misc/icons/545560/ex.svg
@@ -0,0 +1 @@
+<svg width="16" height="16" viewBox="0 0 16 16" fill="none" xmlns="http://www.w3.org/2000/svg"><path d="M2.34351 2.34283L13.6572 13.6565" stroke="#55565B" stroke-width="3"/><path d="M2.34351 13.6572L13.6572 2.34349" stroke="#55565B" stroke-width="3"/></svg>
diff --git a/core/misc/icons/545560/pencil.svg b/core/misc/icons/545560/pencil.svg
new file mode 100644
index 0000000000..2808993ddf
--- /dev/null
+++ b/core/misc/icons/545560/pencil.svg
@@ -0,0 +1 @@
+<svg xmlns="http://www.w3.org/2000/svg" width="16" height="16"><g><path fill="#545560" d="M14.545 3.042l-1.586-1.585c-.389-.389-1.025-.389-1.414 0l-1.293 1.293 3 3 1.293-1.293c.389-.389.389-1.026 0-1.415z"/><rect fill="#545560" x="5.129" y="3.8" transform="matrix(-.707 -.707 .707 -.707 6.189 20.064)" width="4.243" height="9.899"/><path fill="#545560" d="M.908 14.775c-.087.262.055.397.316.312l2.001-.667-1.65-1.646-.667 2.001z"/></g></svg>
diff --git a/core/themes/claro/claro.libraries.yml b/core/themes/claro/claro.libraries.yml
index d4fbca8419..492044d1c2 100644
--- a/core/themes/claro/claro.libraries.yml
+++ b/core/themes/claro/claro.libraries.yml
@@ -186,6 +186,12 @@ checkbox:
   dependencies:
     - core/drupal
 
+icon-link:
+  version: VERSION
+  css:
+    component:
+      css/components/icon-link.css: {}
+
 dropbutton:
   version: VERSION
   js:
@@ -258,6 +264,8 @@ media_library.theme:
   css:
     theme:
       css/theme/media-library.css: {}
+  dependencies:
+    - claro/icon-link
 
 media_library.ui:
   version: VERSION
diff --git a/core/themes/claro/claro.theme b/core/themes/claro/claro.theme
index 5d735acb6b..8588d07bea 100644
--- a/core/themes/claro/claro.theme
+++ b/core/themes/claro/claro.theme
@@ -639,7 +639,7 @@ function claro_views_ui_display_tab_alter(&$element) {
 }
 
 /**
- * Implements hook_preprocess_HOOK for views_exposed_form.
+ * Implements hook_preprocess_HOOK() for views_exposed_form.
  */
 function claro_preprocess_views_exposed_form(&$variables) {
   $form = &$variables['form'];
@@ -1263,7 +1263,11 @@ function claro_form_media_library_add_form_alter(array &$form, FormStateInterfac
  */
 function claro_form_media_library_add_form_upload_alter(array &$form, FormStateInterface $form_state) {
   $form['#attributes']['class'][] = 'media-library-add-form--upload';
-
+  $form['#attributes']['class'][] = 'form--small';
+  if (isset($form['container']['upload'])) {
+    // Set this flag so we can remove the details element.
+    $form['container']['upload']['#do_not_wrap_in_details'] = TRUE;
+  }
   if (isset($form['container'])) {
     $form['container']['#attributes']['class'][] = 'media-library-add-form__input-wrapper';
   }
@@ -1274,6 +1278,7 @@ function claro_form_media_library_add_form_upload_alter(array &$form, FormStateI
  */
 function claro_form_media_library_add_form_oembed_alter(array &$form, FormStateInterface $form_state) {
   $form['#attributes']['class'][] = 'media-library-add-form--oembed';
+  $form['#attributes']['class'][] = 'form--small';
 
   // If no media items have been added yet, add a couple of styling classes
   // to the initial URL form.
@@ -1291,15 +1296,22 @@ function claro_form_media_library_add_form_oembed_alter(array &$form, FormStateI
  * they are saved.
  */
 function claro_preprocess_item_list__media_library_add_form_media_list(array &$variables) {
+  $variables['attributes']['class'][] = 'form--small';
+
   foreach ($variables['items'] as &$item) {
     $item['value']['preview']['#attributes']['class'][] = 'media-library-add-form__preview';
     $item['value']['fields']['#attributes']['class'][] = 'media-library-add-form__fields';
     $item['value']['remove_button']['#attributes']['class'][] = 'media-library-add-form__remove-button';
+    $item['value']['remove_button']['#attributes']['class'][] = 'button--extrasmall';
 
     // #source_field_name is set by AddFormBase::buildEntityFormElement()
     // to help themes and form_alter hooks identify the source field.
     $fields = &$item['value']['fields'];
     $source_field_name = $fields['#source_field_name'];
+
+    // Set this flag so we can remove the details element.
+    $fields[$source_field_name]['widget'][0]['#do_not_wrap_in_details'] = TRUE;
+
     if (isset($fields[$source_field_name])) {
       $fields[$source_field_name]['#attributes']['class'][] = 'media-library-add-form__source-field';
     }
@@ -1313,6 +1325,7 @@ function claro_preprocess_item_list__media_library_add_form_media_list(array &$v
  */
 function claro_preprocess_media_library_item__widget(array &$variables) {
   $variables['content']['remove_button']['#attributes']['class'][] = 'media-library-item__remove';
+  $variables['content']['remove_button']['#attributes']['class'][] = 'icon-link';
 }
 
 /**
@@ -1333,6 +1346,9 @@ function claro_preprocess_media_library_item__small(array &$variables) {
  */
 function claro_preprocess_fieldset__media_library_widget(array &$variables) {
   if (isset($variables['prefix']['weight_toggle'])) {
+    $variables['prefix']['weight_toggle']['#attributes']['class'][] = 'action-link';
+    $variables['prefix']['weight_toggle']['#attributes']['class'][] = 'action-link--extrasmall';
+    $variables['prefix']['weight_toggle']['#attributes']['class'][] = 'action-link--icon-show';
     $variables['prefix']['weight_toggle']['#attributes']['class'][] = 'media-library-widget__toggle-weight';
   }
   if (isset($variables['suffix']['open_button'])) {
@@ -1368,9 +1384,11 @@ function claro_views_pre_render(ViewExecutable $view) {
       }
       if (array_key_exists('edit_media', $view->field)) {
         $add_classes($view->field['edit_media']->options['alter']['link_class'], ['media-library-item__edit']);
+        $add_classes($view->field['edit_media']->options['alter']['link_class'], ['icon-link']);
       }
       if (array_key_exists('delete_media', $view->field)) {
         $add_classes($view->field['delete_media']->options['alter']['link_class'], ['media-library-item__remove']);
+        $add_classes($view->field['delete_media']->options['alter']['link_class'], ['icon-link']);
       }
     }
     elseif (strpos($view->current_display, 'widget') === 0) {
@@ -1402,6 +1420,9 @@ function claro_views_pre_render(ViewExecutable $view) {
  */
 function claro_preprocess_links__media_library_menu(array &$variables) {
   foreach ($variables['links'] as &$link) {
+    // Add a class to the Media Library menu items.
+    $link['attributes']->addClass('media-library-menu__item');
+
     // This conditional exists because the media-library-menu__link class is
     // currently added by Classy, but Claro will eventually not use Classy as a
     // base theme.
diff --git a/core/themes/claro/css/base/variables.css b/core/themes/claro/css/base/variables.css
index 69dc17481c..b46c66a547 100644
--- a/core/themes/claro/css/base/variables.css
+++ b/core/themes/claro/css/base/variables.css
@@ -49,4 +49,7 @@
   /**
    * Breadcrumb.
    */
+  /**
+    * Vertical Tabs.
+    */
 }
diff --git a/core/themes/claro/css/base/variables.pcss.css b/core/themes/claro/css/base/variables.pcss.css
index c0987bb801..a2913302e5 100644
--- a/core/themes/claro/css/base/variables.pcss.css
+++ b/core/themes/claro/css/base/variables.pcss.css
@@ -196,4 +196,26 @@
    * Breadcrumb.
    */
   --breadcrumb-height: 1.25rem;
+  /**
+    * Vertical Tabs.
+    */
+  --vertical-tabs-margin-vertical: var(--space-s);
+  --vertical-tabs-border-radius: var(--details-accordion-border-size-radius);
+  --vertical-tabs-shadow: var(--details-box-shadow);
+  --vertical-tabs-border-color: var(--details-border-color);
+  --vertical-tabs-border-size: 1px;
+  --vertical-tabs-border: var(--vertical-tabs-border-size) solid var(--vertical-tabs-border-color);
+  --vertical-tabs-menu-item-shadow-extraspace: 0.5rem;
+  --vertical-tabs-menu-item--top-margin: calc(var(--vertical-tabs-menu-item-shadow-extraspace) * -2);
+  --vertical-tabs-menu-item--right-margin: calc(var(--vertical-tabs-border-size) * -1);
+  --vertical-tabs-menu-item--bottom-margin: calc(var(--vertical-tabs-menu-item-shadow-extraspace) * -1);
+  --vertical-tabs-menu-item--left-margin: calc(var(--vertical-tabs-menu-item-shadow-extraspace) * -1);
+  --vertical-tabs-menu-separator-color: var(--color-lightgray);
+  --vertical-tabs-menu-separator-size: 1px;
+  --vertical-tabs-menu-width: 20em;
+  --vertical-tabs-pane-width: calc(100% - var(--vertical-tabs-menu-width));
+  --vertical-tabs-menu-link-focus-border-size: var(--details-summary-focus-border-size);
+  --vertical-tabs-menu-link--active-border-size: 4px;
+  --vertical-tabs-menu-link--active-border-color: var(--color-absolutezero);
+  --vertical-tabs-menu--z-index: 0;
 }
diff --git a/core/themes/claro/css/components/action-link.css b/core/themes/claro/css/components/action-link.css
index f573a6684e..6d1eb9a30e 100644
--- a/core/themes/claro/css/components/action-link.css
+++ b/core/themes/claro/css/components/action-link.css
@@ -57,6 +57,9 @@
   /**
    * Breadcrumb.
    */
+  /**
+    * Vertical Tabs.
+    */
 }
 
 /**
diff --git a/core/themes/claro/css/components/autocomplete-loading.module.css b/core/themes/claro/css/components/autocomplete-loading.module.css
index f4e79323ca..88255479a2 100644
--- a/core/themes/claro/css/components/autocomplete-loading.module.css
+++ b/core/themes/claro/css/components/autocomplete-loading.module.css
@@ -57,6 +57,9 @@
   /**
    * Breadcrumb.
    */
+  /**
+    * Vertical Tabs.
+    */
 }
 
 /**
diff --git a/core/themes/claro/css/components/button.css b/core/themes/claro/css/components/button.css
index ffe9155cb5..d03120fb71 100644
--- a/core/themes/claro/css/components/button.css
+++ b/core/themes/claro/css/components/button.css
@@ -57,6 +57,9 @@
   /**
    * Breadcrumb.
    */
+  /**
+    * Vertical Tabs.
+    */
 }
 
 /**
diff --git a/core/themes/claro/css/components/form--select.css b/core/themes/claro/css/components/form--select.css
index 063e96077c..30ff31dffe 100644
--- a/core/themes/claro/css/components/form--select.css
+++ b/core/themes/claro/css/components/form--select.css
@@ -55,6 +55,9 @@
   /**
    * Breadcrumb.
    */
+  /**
+    * Vertical Tabs.
+    */
 }
 
 .form-element--type-select {
diff --git a/core/themes/claro/css/components/form--text.css b/core/themes/claro/css/components/form--text.css
index a4ec1ca5e4..fa244d1afe 100644
--- a/core/themes/claro/css/components/form--text.css
+++ b/core/themes/claro/css/components/form--text.css
@@ -55,6 +55,9 @@
   /**
    * Breadcrumb.
    */
+  /**
+    * Vertical Tabs.
+    */
 }
 
 .form-element {
diff --git a/core/themes/claro/css/components/icon-link.css b/core/themes/claro/css/components/icon-link.css
new file mode 100644
index 0000000000..95ddafcaa5
--- /dev/null
+++ b/core/themes/claro/css/components/icon-link.css
@@ -0,0 +1,94 @@
+/*
+ * DO NOT EDIT THIS FILE.
+ * See the following change record for more information,
+ * https://www.drupal.org/node/3084859
+ * @preserve
+ */
+
+/**
+ * @file
+ * Icon link component.
+ */
+
+:root {
+  /*
+   * Color Palette.
+   */
+  /* Secondary. */
+  /* Variations. */ /* 5% darker than base. */ /* 10% darker than base. */ /* 10% darker than base. */ /* 20% darker than base. */ /* 5% darker than base. */ /* 10% darker than base. */ /* 5% darker than base. */ /* 10% darker than base. */ /* 5% darker than base. */ /* 10% darker than base. */
+  /*
+   * Base.
+   */
+  /*
+   * Typography.
+   */ /* 1rem = 16px if font root is 100% ands browser defaults are used. */ /* ~32px */ /* ~29px */ /* ~26px */ /* ~23px */ /* ~20px */ /* 18px */ /* ~14px */ /* ~13px */ /* ~11px */
+  /**
+   * Spaces.
+   */ /* 3 * 16px = 48px */ /* 1.5 * 16px = 24px */ /* 1 * 16px = 16px */ /* 0.75 * 16px = 12px */ /* 0.5 * 16px = 8px */
+  /*
+   * Common.
+   */
+  /*
+   * Inputs.
+   */ /* Absolute zero with opacity. */ /* Davy's gray with 0.6 opacity. */ /* Light gray with 0.3 opacity on white bg. */ /* Old silver with 0.5 opacity on white bg. */ /* (1/8)em ~ 2px */ /* (1/16)em ~ 1px */ /* Font size is too big to use 1rem for extrasmall line-height */ /* 7px inside the form element label. */ /* 8px with the checkbox width of 19px */
+  /*
+   * Details.
+   */
+  /**
+   * Buttons.
+   */
+  /**
+   * jQuery.UI dropdown.
+   */ /* Light gray with 0.8 opacity. */ /* Text color with 0.1 opacity. */
+  /**
+   * jQuery.UI dialog.
+   */
+  /**
+   * Progress bar.
+   */
+  /**
+   * Tabledrag icon size.
+   */ /* 17px */
+  /**
+   * Ajax progress.
+   */
+  /**
+   * Breadcrumb.
+   */
+  /**
+    * Vertical Tabs.
+    */
+}
+
+:root {
+  /* default */
+  /* active */
+  /* hover */
+}
+
+.icon-link {
+  display: flex;
+  padding: 0;
+  border: 1px solid #d4d4d8;
+  border-radius: 50%;
+  background-color: #fff;
+}
+
+.icon-link:hover {
+  border-color: rgba(212, 212, 218, 0.8);
+  background-color: #f0f5fd;
+}
+
+.icon-link:focus {
+  box-shadow: 0 0 0 1.5px #fff, 0 0 0 3.5px #26a769;
+}
+
+.icon-link:active,
+.open > .icon-link {
+  border-color: #003cc5;
+  background-color: #003cc5;
+}
+
+.icon-link--small:focus {
+  box-shadow: 0 0 0 1px #fff, 0 0 0 3px #26a769;
+}
diff --git a/core/themes/claro/css/components/icon-link.pcss.css b/core/themes/claro/css/components/icon-link.pcss.css
new file mode 100644
index 0000000000..cdbfc8e685
--- /dev/null
+++ b/core/themes/claro/css/components/icon-link.pcss.css
@@ -0,0 +1,45 @@
+/**
+ * @file
+ * Icon link component.
+ */
+
+@import "../base/variables.pcss.css";
+
+:root {
+  /* default */
+  --icon-link-bg-color: var(--color-white);
+  --icon-link-border-color: var(--color-lightgray);
+  /* active */
+  --icon-link--active-bg-color: var(--color-absolutezero);
+  --icon-link--active-border-color: var(--color-absolutezero);
+  /* hover */
+  --icon-link--hover-bg-color: var(--color-bgblue-hover);
+  --icon-link--hover-border-color: var(--color-lightgray-o-80);
+}
+
+.icon-link {
+  display: flex;
+  padding: 0;
+  border: 1px solid var(--icon-link-border-color);
+  border-radius: 50%;
+  background-color: var(--icon-link-bg-color);
+}
+
+.icon-link:hover {
+  border-color: var(--icon-link--hover-border-color);
+  background-color: var(--icon-link--hover-bg-color);
+}
+
+.icon-link:focus {
+  box-shadow: 0 0 0 1.5px var(--color-white), 0 0 0 3.5px var(--color-focus);
+}
+
+.icon-link:active,
+.open > .icon-link {
+  border-color: var(--icon-link--active-border-color);
+  background-color: var(--icon-link--active-bg-color);
+}
+
+.icon-link--small:focus {
+  box-shadow: 0 0 0 1px var(--color-white), 0 0 0 3px var(--color-focus);
+}
diff --git a/core/themes/claro/css/components/vertical-tabs.css b/core/themes/claro/css/components/vertical-tabs.css
index 7e939da826..dd2716a1a3 100644
--- a/core/themes/claro/css/components/vertical-tabs.css
+++ b/core/themes/claro/css/components/vertical-tabs.css
@@ -57,6 +57,9 @@
   /**
    * Breadcrumb.
    */
+  /**
+    * Vertical Tabs.
+    */
 }
 
 /**
diff --git a/core/themes/claro/css/components/vertical-tabs.pcss.css b/core/themes/claro/css/components/vertical-tabs.pcss.css
index 12ed6a8647..3410a989b0 100644
--- a/core/themes/claro/css/components/vertical-tabs.pcss.css
+++ b/core/themes/claro/css/components/vertical-tabs.pcss.css
@@ -7,23 +7,6 @@
 
 @import "../base/variables.pcss.css";
 
-:root {
-  --vertical-tabs-margin-vertical: var(--space-s);
-  --vertical-tabs-border-radius: var(--details-accordion-border-size-radius);
-  --vertical-tabs-shadow: var(--details-box-shadow);
-  --vertical-tabs-border-color: var(--details-border-color);
-  --vertical-tabs-border-size: 1px;
-  --vertical-tabs-border: var(--vertical-tabs-border-size) solid var(--vertical-tabs-border-color);
-  --vertical-tabs-menu-item-shadow-extraspace: 0.5rem;
-  --vertical-tabs-menu-separator-color: var(--color-lightgray);
-  --vertical-tabs-menu-separator-size: 1px;
-  --vertical-tabs-menu-width: 20em;
-  --vertical-tabs-pane-width: calc(100% - var(--vertical-tabs-menu-width));
-  --vertical-tabs-menu-link-focus-border-size: var(--details-summary-focus-border-size);
-  --vertical-tabs-menu-link--active-border-size: 4px;
-  --vertical-tabs-menu-link--active-border-color: var(--color-absolutezero);
-}
-
 /**
  * Main wrapper of vertical tabs.
  * This wrapper div is added by JavaScript.
@@ -70,12 +53,12 @@
  */
 .vertical-tabs__menu-item {
   overflow: hidden;
-  margin: calc(var(--vertical-tabs-menu-item-shadow-extraspace) * -2) calc(var(--vertical-tabs-border-size) * -1) calc(var(--vertical-tabs-menu-item-shadow-extraspace) * -1) calc(var(--vertical-tabs-menu-item-shadow-extraspace) * -1); /* LTR */
+  margin: var(--vertical-tabs-menu-item--top-margin) var(--vertical-tabs-menu-item--right-margin) var(--vertical-tabs-menu-item--bottom-margin) var(--vertical-tabs-menu-item--left-margin); /* LTR */
   padding: var(--vertical-tabs-menu-item-shadow-extraspace) 0 var(--vertical-tabs-menu-item-shadow-extraspace) var(--vertical-tabs-menu-item-shadow-extraspace); /* LTR */
 }
 [dir="rtl"] .vertical-tabs__menu-item {
-  margin-right: calc(var(--vertical-tabs-menu-item-shadow-extraspace) * -1);
-  margin-left: calc(var(--vertical-tabs-border-size) * -1);
+  margin-right: var(--vertical-tabs-menu-item--left-margin);
+  margin-left: var(--vertical-tabs-menu-item--right-margin);
   padding-right: var(--vertical-tabs-menu-item-shadow-extraspace);
   padding-left: 0;
 }
diff --git a/core/themes/claro/css/components/views-exposed-form.css b/core/themes/claro/css/components/views-exposed-form.css
index 71fffe4879..1df4a275e3 100644
--- a/core/themes/claro/css/components/views-exposed-form.css
+++ b/core/themes/claro/css/components/views-exposed-form.css
@@ -55,6 +55,9 @@
   /**
    * Breadcrumb.
    */
+  /**
+    * Vertical Tabs.
+    */
 }
 
 /**
diff --git a/core/themes/claro/css/theme/media-library.css b/core/themes/claro/css/theme/media-library.css
index 4724c8473e..16f3e119fe 100644
--- a/core/themes/claro/css/theme/media-library.css
+++ b/core/themes/claro/css/theme/media-library.css
@@ -11,9 +11,70 @@
  * Styling for Media Library.
  */
 
+:root {
+  /*
+   * Color Palette.
+   */
+  /* Secondary. */
+  /* Variations. */ /* 5% darker than base. */ /* 10% darker than base. */ /* 10% darker than base. */ /* 20% darker than base. */ /* 5% darker than base. */ /* 10% darker than base. */ /* 5% darker than base. */ /* 10% darker than base. */ /* 5% darker than base. */ /* 10% darker than base. */
+  /*
+   * Base.
+   */
+  /*
+   * Typography.
+   */ /* 1rem = 16px if font root is 100% ands browser defaults are used. */ /* ~32px */ /* ~29px */ /* ~26px */ /* ~23px */ /* ~20px */ /* 18px */ /* ~14px */ /* ~13px */ /* ~11px */
+  /**
+   * Spaces.
+   */ /* 3 * 16px = 48px */ /* 1.5 * 16px = 24px */ /* 1 * 16px = 16px */ /* 0.75 * 16px = 12px */ /* 0.5 * 16px = 8px */
+  /*
+   * Common.
+   */
+  /*
+   * Inputs.
+   */ /* Absolute zero with opacity. */ /* Davy's gray with 0.6 opacity. */ /* Light gray with 0.3 opacity on white bg. */ /* Old silver with 0.5 opacity on white bg. */ /* (1/8)em ~ 2px */ /* (1/16)em ~ 1px */ /* Font size is too big to use 1rem for extrasmall line-height */ /* 7px inside the form element label. */ /* 8px with the checkbox width of 19px */
+  /*
+   * Details.
+   */
+  /**
+   * Buttons.
+   */
+  /**
+   * jQuery.UI dropdown.
+   */ /* Light gray with 0.8 opacity. */ /* Text color with 0.1 opacity. */
+  /**
+   * jQuery.UI dialog.
+   */
+  /**
+   * Progress bar.
+   */
+  /**
+   * Tabledrag icon size.
+   */ /* 17px */
+  /**
+   * Ajax progress.
+   */
+  /**
+   * Breadcrumb.
+   */
+  /**
+    * Vertical Tabs.
+    */
+}
+
 .media-library-wrapper {
   display: flex;
-  margin: -1em;
+  margin: -1em -1.5em -1em -1em;
+}
+
+[dir="rtl"] .media-library-wrapper {
+  margin-right: -1em;
+  margin-left: -1.5em;
+}
+
+.media-library-wrapper .messages-list,
+.media-library-wrapper .messages {
+  margin-top: 0;
+  margin-bottom: 1.5rem;
 }
 
 /**
@@ -22,17 +83,18 @@
  */
 
 .media-library-menu {
+  position: relative;
   display: block;
-  width: 600px;
-  max-width: 20%;
-  margin: 0; /* LTR */
-  padding: 0;
-  border-bottom: 1px solid #ccc;
-  background-color: #e6e5e1;
-  line-height: 1;
+  float: left; /* LTR */
+  width: 20em;
+  margin: 0;
+  padding-top: 0.5rem;
+  list-style: none;
+  color: #222330;
 }
 
 [dir="rtl"] .media-library-menu {
+  float: right;
   margin: 0;
 }
 
@@ -41,68 +103,164 @@
  *   https://www.drupal.org/project/drupal/issues/3029227
  */
 
-.media-library-menu li {
+.media-library-menu__item {
+  overflow: hidden;
+  margin: -1rem -1px -0.5rem -0.5rem; /* LTR */
+  padding: 0.5rem 0; /* LTR */
+}
+
+[dir="rtl"] .media-library-menu__item {
+  margin-right: -0.5rem;
+  margin-left: -1px;
+}
+
+.media-library-menu__item::before {
+  z-index: 0; /* The line should be kept above the vertical tabs menu link to keep it visible even if the link is hovered and gets the 'hover' background color. */
   display: block;
-  padding: 0;
-  list-style: none;
+  width: 100%;
+  margin-top: -1px;
+  content: "";
+  border-top: 1px solid #d4d4d8;
 }
 
 .media-library-menu__link {
   position: relative;
   display: block;
-  box-sizing: border-box;
-  padding: 15px;
+  margin-top: -1px;
+  padding: 0.75rem 0.75rem 0.75rem calc(1.5rem - 4px); /* LTR */
   text-decoration: none;
-  border-bottom: 1px solid #b3b2ad;
-  background-color: #f2f2f0;
-  text-shadow: 0 1px hsla(0, 0%, 100%, 0.6);
+  word-wrap: break-word;
+  -webkit-hyphens: auto;
+  -ms-hyphens: auto;
+  hyphens: auto;
+  color: #222330;
+  border: 1px solid transparent;
+  border-width: 1px 0 1px 4px; /* LTR */
+  border-radius: 2px 0 0 2px; /* LTR */
+}
+
+[dir="rtl"] .media-library-menu__link {
+  padding-right: calc(1.5rem - 4px);
+  padding-left: 0.75rem;
+  border-width: 1px 4px 1px 0;
+  border-radius: 0 2px 2px 0;
+}
+
+@media screen and (-ms-high-contrast: active) {
+  .media-library-menu__link {
+    border-color: transparent;
+  }
 }
 
-.media-library-menu__link:active,
-.media-library-menu__link:hover,
+/* Menu link states. */
+
 .media-library-menu__link:focus {
-  background: #fcfcfa;
-  text-shadow: none;
+  z-index: 3; /* Focus state should be on the highest level to make the focus effect be fully visible. This also means that it should have bigger z-index than the selected link. */
+  text-decoration: none;
+  box-shadow: none;
 }
 
-.media-library-menu__link:focus,
-.media-library-menu__link:active {
-  outline: none;
+.media-library-menu__link:hover {
+  text-decoration: none;
+  color: #003cc5;
+  /* These borders are necessary to replace the dividing lines while in the hover state. */
+  border-top: 1px solid #d4d4d8;
+  border-bottom: 1px solid #d4d4d8;
+  background: #f0f5fd;
+}
+
+/* This pseudo element provides the background for the hover state. */
+
+.media-library-menu__link::before {
+  position: absolute;
+  z-index: -1; /* This should be on a lower level than the menu-item separator lines. */
+  top: -1px;
+  right: 0; /* LTR */
+  bottom: -1px;
+  left: -4px; /* LTR */
+  content: "";
+  pointer-events: none;
+  background-clip: padding-box;
+}
+
+[dir="rtl"] .media-library-menu__link::before {
+  right: -4px;
+  left: 0;
+}
+
+.media-library-menu__link:focus::after {
+  position: absolute;
+  top: 0;
+  right: 0;
+  bottom: 0;
+  left: 0;
+  margin: -1px -4px;
+  content: "";
+  pointer-events: none;
+  border: 3px solid #26a769;
+  border-radius: 2px;
 }
 
 .media-library-menu__link.active {
-  z-index: 1;
-  margin-right: -1px; /* LTR */
-  color: #000;
-  border-right: 1px solid #fcfcfa; /* LTR */
-  border-bottom: 1px solid #b3b2ad;
+  z-index: 2; /* The selected menu link should be on a higher level than the white masking line that hides the grey separator. */
+  color: #003cc5;
+  border-color: rgba(216, 217, 224, 0.8) transparent;
   background-color: #fff;
-  box-shadow: 0 5px 5px -5px hsla(0, 0%, 0%, 0.3);
+  box-shadow: 0
+2px
+4px
+rgba(0, 0, 0, 0.1);
 }
 
-[dir="rtl"] .media-library-menu__link.active {
-  margin-right: 0;
-  margin-left: -1px;
-  border-right: 0;
-  border-left: 1px solid #fcfcfa;
+.media-library-menu__link.active:hover {
+  color: #0036b1;
+  background-color: #f0f5fd;
+}
+
+.media-library-menu__link.active::before {
+  z-index: 1; /* The blue active-tab indication should be on a higher level than the green focus border. */
+  border-left: 4px solid #003cc5; /* LTR */
+  border-radius: 2px 0 0 2px; /* LTR */
+}
+
+[dir=rtl] .media-library-menu__link.active::before {
+  border-right: 4px solid #003cc5;
+  border-left: 0;
+  border-radius: 0 2px 2px 0;
+}
+
+.media-library-menu__link.active:hover::before {
+  background: none;
 }
 
 .media-library-content {
   width: 100%;
   padding: 1em;
-  border-left: 1px solid #b3b2ad; /* LTR */
   outline: none;
 }
 
-[dir="rtl"] .media-library-content {
-  border-right: 1px solid #b3b2ad;
+.media-library-menu + .media-library-content {
+  z-index: 0;
+  border-left: 1px
+solid
+rgba(216, 217, 224, 0.8); /* LTR */
+  box-shadow: 0
+2px
+4px
+rgba(0, 0, 0, 0.1);
+}
+
+[dir="rtl"] .media-library-menu + .media-library-content {
+  border-right: 1px
+solid
+rgba(216, 217, 224, 0.8);
   border-left: 0;
 }
 
 /* Generic media add form styles. */
 
 .media-library-add-form--without-input .form-item {
-  margin: 0 0 1em;
+  margin-right: 1rem;
 }
 
 /**
@@ -118,11 +276,30 @@
   outline: none;
 }
 
+/* This Media Library form is an exception to the extrasmall button pattern. */
+
+.media-library-add-form__added-media .media-library-add-form__remove-button.button--extrasmall {
+  margin: 0.5rem 0; /* LTR */
+  /* Left padding is double the background size of the button icon. */
+  padding: calc(0.25rem - 1px) calc(0.75rem - 1px) calc(0.25rem - 1px) 1.5rem;
+}
+
+/* This is needed to override the default extrasmall button left margin. */
+
+[dir="rtl"] .media-library-add-form__added-media .media-library-add-form__remove-button.button--extrasmall {
+  margin-left: 0;
+}
+
 .media-library-add-form__input-wrapper {
-  padding: 16px;
-  border: 1px solid #bfbfbf;
+  padding: 0.5rem 1.5rem 1.5rem 1.5rem;
+  border: 1px solid rgba(216, 217, 224, 0.8);
   border-radius: 2px;
-  background: #fcfcfa;
+  background-color: #fff;
+  box-shadow: 0
+2px
+4px
+rgba(0, 0, 0, 0.1);
+  /* background: #fcfcfa; */
 }
 
 /* Style the media add upload form. */
@@ -131,14 +308,41 @@
   margin-bottom: 0;
 }
 
+.media-library-add-form--upload.media-library-add-form--with-input .form-managed-file_meta {
+  margin-top: 0;
+}
+
+.media-library-add-form--upload.media-library-add-form--with-input .form-managed-file__main,
+.media-library-add-form--upload.media-library-add-form--with-input .form-managed-file.no-upload {
+  display: block;
+}
+
+/* Adjust the focus border on this element so it is not too close to buttons. */
+
+.media-library-add-form__added-media:focus {
+  box-shadow: 0 0 0 4px #fff, 0 0 0 7px #26a769;
+}
+
 .media-library-add-form .file-upload-help {
   margin: 8px 0 0;
 }
 
+/* Align remove buttons with with Save button and compensate for IE scrollbar and focus padding. */
+
+@media all and (-ms-high-contrast: active), (-ms-high-contrast: none) {
+  .ui-dialog > .ui-dialog-content {
+    padding-right: calc(0.75rem - 7px);
+  }
+  [dir="rtl"] .ui-dialog > .ui-dialog-content {
+    padding-left: calc(0.75rem - 7px);
+  }
+}
+
 /* Style the media add oEmbed form. */
 
 .media-library-add-form--oembed .media-library-add-form__input-wrapper {
   display: flex;
+  align-items: center;
 }
 
 @media screen and (max-width: 37.5em) {
@@ -279,7 +483,7 @@
 
 .media-library-wrapper .views-display-link-widget {
   margin-right: 15px;
-  background: url("data:image/svg+xml,%3csvg xmlns='http://www.w3.org/2000/svg' width='16' height='16'%3e%3cpath fill='%23333333' d='M10.5 9h3a1.5 1.5 0 0 1 1.5 1.5v3a1.5 1.5 0 0 1-1.5 1.5h-3A1.5 1.5 0 0 1 9 13.5v-3A1.5 1.5 0 0 1 10.5 9zm-8 0h3A1.5 1.5 0 0 1 7 10.5v3A1.5 1.5 0 0 1 5.5 15h-3A1.5 1.5 0 0 1 1 13.5v-3A1.5 1.5 0 0 1 2.5 9zm8-8h3A1.5 1.5 0 0 1 15 2.5v3A1.5 1.5 0 0 1 13.5 7h-3A1.5 1.5 0 0 1 9 5.5v-3A1.5 1.5 0 0 1 10.5 1zm-8 0h3A1.5 1.5 0 0 1 7 2.5v3A1.5 1.5 0 0 1 5.5 7h-3A1.5 1.5 0 0 1 1 5.5v-3A1.5 1.5 0 0 1 2.5 1z'/%3e%3c/svg%3e") left 0 no-repeat; /* LTR */
+  background: url(../../../../misc/icons/333333/grid.svg) left 0 no-repeat; /* LTR */
 }
 
 [dir="rtl"] .media-library-wrapper .views-display-link-widget {
@@ -287,7 +491,7 @@
 }
 
 .media-library-wrapper .views-display-link-widget_table {
-  background: url("data:image/svg+xml,%3csvg xmlns='http://www.w3.org/2000/svg' width='16' height='16'%3e%3cpath fill='%23333333' d='M7 15a1.5 1.5 0 0 1 0-3h7a1.5 1.5 0 0 1 0 3H7zm-4.5 0a1.5 1.5 0 1 1 0-3 1.5 1.5 0 0 1 0 3zM7 9.5a1.5 1.5 0 0 1 0-3h7a1.5 1.5 0 0 1 0 3H7zm-4.5 0a1.5 1.5 0 1 1 0-3 1.5 1.5 0 0 1 0 3zM7 4a1.5 1.5 0 0 1 0-3h7a1.5 1.5 0 0 1 0 3H7zM2.5 4a1.5 1.5 0 1 1 0-3 1.5 1.5 0 0 1 0 3z'/%3e%3c/svg%3e") left 0 no-repeat; /* LTR */
+  background: url(../../../../misc/icons/333333/table.svg) left 0 no-repeat; /* LTR */
 }
 
 [dir="rtl"] .media-library-wrapper .views-display-link-widget_table {
@@ -302,6 +506,40 @@
   position: relative;
 }
 
+/**
+ * Ajax throbbers inside a media library item.
+ */
+
+.media-library-item .ajax-progress.ajax-progress.ajax-progress {
+  position: absolute;
+  z-index: 1;
+  top: 50%;
+  left: 50%;
+  box-sizing: border-box;
+  width: 3rem; /* 56px */
+  height: 3rem;
+  margin: -1.5rem;
+  border: 1px solid rgba(216, 217, 224, 0.8);
+  border-radius: 3.5rem;
+  background: #fff;
+  box-shadow: 0 0.25rem 0.625rem rgba(34, 35, 48, 0.1);
+}
+
+.media-library-item .ajax-progress__throbber {
+  position: absolute;
+  top: 50%;
+  left: 50%;
+  width: 1.75rem;
+  height: 1.75rem;
+  margin: -0.875rem;
+  border: 3px solid #003cc5;
+  border-right: 3px dotted transparent;
+}
+
+.media-library-item .ajax-progress__message {
+  display: none;
+}
+
 /**
 * The media library item container receives screen reader focus when items are
 * removed. Since it is not an interactive element, it does not need an
@@ -318,6 +556,10 @@
   background: #fff;
 }
 
+.media-library-item--grid:focus {
+  box-shadow: none;
+}
+
 .media-library-item--grid:before {
   position: absolute;
   top: 7px;
@@ -328,6 +570,11 @@
   transition: border-color 0.2s, color 0.2s, background 0.2s;
   pointer-events: none;
   border: 1px solid #dbdbdb;
+  border-radius: 2px;
+  box-shadow: 0
+2px
+4px
+rgba(0, 0, 0, 0.1);
 }
 
 /* Media library widget weight field styles. */
@@ -431,12 +678,20 @@
   top: 5px;
   left: 5px;
   border-width: 3px;
-  border-color: #40b6ff;
   border-radius: 3px;
 }
 
+.media-library-item--grid.is-hover:before,
+.media-library-item--grid.checked.is-hover:before {
+  border-color: #0036b1;
+}
+
+.media-library-item--grid.is-focus:before {
+  border-color: #26a769;
+}
+
 .media-library-item--grid.checked:before {
-  border-color: #0076c0;
+  border-color: #003cc5;
 }
 
 .media-library-item__click-to-select-checkbox {
@@ -484,6 +739,11 @@
   cursor: move;
 }
 
+.field--widget-media-library-widget .media-library-item__preview img {
+  border-top-left-radius: 2px;
+  border-top-right-radius: 2px;
+}
+
 .field--widget-media-library-widget .js-media-library-item:only-child .media-library-item__preview {
   cursor: inherit;
 }
@@ -516,16 +776,13 @@
   background: white;
 }
 
-.media-library-item__name {
-  font-size: 14px;
-}
-
 .media-library-item__name {
   display: block;
   overflow: hidden;
-  margin: 2px;
+  margin: 0.25rem 0.5rem;
   white-space: nowrap;
   text-overflow: ellipsis;
+  font-size: 14px;
 }
 
 .media-library-item__attributes:hover .media-library-item__name,
@@ -565,15 +822,16 @@
   margin-left: 1em;
 }
 
-.media-library-widget__toggle-weight {
+.media-library-widget__toggle-weight.media-library-widget__toggle-weight {
   position: absolute;
-  top: 5px;
-  right: 5px; /* LTR */
+  top: 0.75rem;
+  right: 1rem; /* LTR */
+  text-decoration: none;
 }
 
-[dir="rtl"] .media-library-widget__toggle-weight {
+[dir="rtl"] .media-library-widget__toggle-weight.media-library-widget__toggle-weight {
   right: auto;
-  left: 5px;
+  left: 1rem;
 }
 
 /* Add negative margin for flex grid. */
@@ -605,15 +863,13 @@
   z-index: 1;
   top: 10px;
   overflow: hidden;
-  width: 21px;
-  height: 21px;
+  width: 24px;
+  height: 24px;
   margin: 5px;
   padding: 0;
   transition: 0.2s border-color;
   color: transparent;
-  border: 2px solid #ccc;
-  border-radius: 20px;
-  background-size: 13px;
+  background-size: 12px;
   text-shadow: none;
   font-size: 0;
 }
@@ -637,8 +893,16 @@
 }
 
 .media-library-item__edit {
-  background: url("data:image/svg+xml,%3csvg xmlns='http://www.w3.org/2000/svg' width='16' height='16'%3e%3cg%3e%3cpath fill='%23787878' d='M14.545 3.042l-1.586-1.585c-.389-.389-1.025-.389-1.414 0l-1.293 1.293 3 3 1.293-1.293c.389-.389.389-1.026 0-1.415z'/%3e%3crect fill='%23787878' x='5.129' y='3.8' transform='matrix(-.707 -.707 .707 -.707 6.189 20.064)' width='4.243' height='9.899'/%3e%3cpath fill='%23787878' d='M.908 14.775c-.087.262.055.397.316.312l2.001-.667-1.65-1.646-.667 2.001z'/%3e%3c/g%3e%3c/svg%3e") #fff center no-repeat;
-  background-size: 13px;
+  /* !important to override button class border. */
+  border: 1px solid #d4d4d8 !important;
+  background-image: url("../../../../misc/icons/545560/pencil.svg");
+  background-repeat: no-repeat;
+  background-position: center;
+  background-size: 12px;
+}
+
+.media-library-item__edit:active {
+  background-image: url("../../../../misc/icons/ffffff/pencil.svg");
 }
 
 .media-library-item__remove,
@@ -648,18 +912,20 @@
 .media-library-item__remove.button:disabled:active,
 .media-library-item__remove.button:hover,
 .media-library-item__remove.button:focus {
-  background: url("data:image/svg+xml,%3csvg xmlns='http://www.w3.org/2000/svg' width='16' height='16'%3e%3cpath fill='%23787878' d='M3.51 13.925c.194.194.512.195.706.001l3.432-3.431c.194-.194.514-.194.708 0l3.432 3.431c.192.194.514.193.707-.001l1.405-1.417c.191-.195.189-.514-.002-.709l-3.397-3.4c-.192-.193-.192-.514-.002-.708l3.401-3.43c.189-.195.189-.515 0-.709l-1.407-1.418c-.195-.195-.513-.195-.707-.001l-3.43 3.431c-.195.194-.516.194-.708 0l-3.432-3.431c-.195-.195-.512-.194-.706.001l-1.407 1.417c-.194.195-.194.515 0 .71l3.403 3.429c.193.195.193.514-.001.708l-3.4 3.399c-.194.195-.195.516-.001.709l1.406 1.419z'/%3e%3c/svg%3e") #fff center no-repeat;
-  background-size: 13px;
+  /* !important to override button class border. */
+  border: 1px solid #d4d4d8 !important;
+  background-image: url("../../../../misc/icons/545560/ex.svg");
+  background-repeat: no-repeat;
+  background-position: center;
+  background-size: 12px;
 }
 
-.media-library-item__edit:hover,
-.media-library-item__edit:focus,
-.media-library-item__remove:hover,
-.media-library-item__remove:focus,
-.media-library-item__remove.button:hover,
-.media-library-item__remove.button:focus,
+.media-library-item__remove:active,
+.media-library-item__remove.button:active,
 .media-library-item__remove.button:disabled:active {
-  border-color: #40b6ff;
+  /* !important to override button class border. */
+  border-color: #003cc5 !important;
+  background-image: url("../../../../misc/icons/ffffff/ex.svg");
 }
 
 /**
@@ -673,28 +939,10 @@
 .media-library-add-form__media {
   position: relative;
   display: flex;
-  padding: 1em 0;
   border-bottom: 1px solid #c0c0c0;
   outline: none;
 }
 
-/* Do not show the top padding for the first item. */
-
-.media-library-add-form__media:first-child {
-  padding-top: 0;
-}
-
-/**
- * Change the position of the remove button for the first item.
- *
- * The first item doesn't have a top padding, change the location of the remove
- * button as well.
- */
-
-.media-library-add-form__media:first-child .media-library-add-form__remove-button[type="submit"] {
-  top: 5px;
-}
-
 /* Do not show the bottom border and padding for the last item. */
 
 .media-library-add-form__media:last-child {
@@ -708,7 +956,7 @@
   justify-content: center;
   width: 220px;
   margin-right: 20px; /* LTR */
-  background: #ebebeb;
+  background: rgba(243, 244, 249, 0.4);
 }
 
 [dir="rtl"] .media-library-add-form__preview {
@@ -720,22 +968,18 @@
   flex-grow: 1;
 }
 
-/**
- * @todo Remove [type="submit"] when styles are moved to the seven theme in
- *   https://www.drupal.org/project/drupal/issues/2980769
- */
-
-.media-library-add-form__remove-button[type="submit"] {
+.media-library-add-form__remove-button {
   position: absolute;
-  top: 25px;
-  right: 6px;
-  margin-right: 0;
+  right: 0;
+  background-image: url("../../../../misc/icons/000000/ex.svg");
+  background-repeat: no-repeat;
+  background-position: 0.5rem center;
+  background-size: 0.75rem;
 }
 
-[dir="rtl"] .media-library-add-form__remove-button[type="submit"] {
+[dir="rtl"] .media-library-add-form__remove-button {
   right: auto;
-  left: 13px;
-  margin-left: 0;
+  left: 0;
 }
 
 /* @todo Remove in https://www.drupal.org/project/drupal/issues/3064914 */
diff --git a/core/themes/claro/css/theme/media-library.pcss.css b/core/themes/claro/css/theme/media-library.pcss.css
index 3ae30c1799..96c4ce336d 100644
--- a/core/themes/claro/css/theme/media-library.pcss.css
+++ b/core/themes/claro/css/theme/media-library.pcss.css
@@ -4,9 +4,21 @@
  * Styling for Media Library.
  */
 
+@import "../base/variables.pcss.css";
+
 .media-library-wrapper {
   display: flex;
-  margin: -1em;
+  margin: -1em -1.5em -1em -1em;
+}
+[dir="rtl"] .media-library-wrapper {
+  margin-right: -1em;
+  margin-left: -1.5em;
+}
+
+.media-library-wrapper .messages-list,
+.media-library-wrapper .messages {
+  margin-top: 0;
+  margin-bottom: var(--space-l);
 }
 
 /**
@@ -14,16 +26,17 @@
  *   https://www.drupal.org/project/drupal/issues/3023767
  */
 .media-library-menu {
+  position: relative;
   display: block;
-  width: 600px;
-  max-width: 20%;
-  margin: 0; /* LTR */
-  padding: 0;
-  border-bottom: 1px solid #ccc;
-  background-color: #e6e5e1;
-  line-height: 1;
+  float: left; /* LTR */
+  width: var(--vertical-tabs-menu-width);
+  margin: 0;
+  padding-top: var(--vertical-tabs-menu-item-shadow-extraspace);
+  list-style: none;
+  color: var(--color-text);
 }
 [dir="rtl"] .media-library-menu {
+  float: right;
   margin: 0;
 }
 
@@ -31,65 +44,147 @@
  * @todo Use a class instead of the li element.
  *   https://www.drupal.org/project/drupal/issues/3029227
  */
-.media-library-menu li {
+.media-library-menu__item {
+  overflow: hidden;
+  margin: var(--vertical-tabs-menu-item--top-margin) var(--vertical-tabs-menu-item--right-margin) var(--vertical-tabs-menu-item--bottom-margin) var(--vertical-tabs-menu-item--left-margin); /* LTR */
+  padding: var(--vertical-tabs-menu-item-shadow-extraspace) 0; /* LTR */
+}
+
+[dir="rtl"] .media-library-menu__item {
+  margin-right: var(--vertical-tabs-menu-item--left-margin);
+  margin-left: var(--vertical-tabs-menu-item--right-margin);
+}
+
+.media-library-menu__item::before {
+  z-index: var(--vertical-tabs-menu--z-index); /* The line should be kept above the vertical tabs menu link to keep it visible even if the link is hovered and gets the 'hover' background color. */
   display: block;
-  padding: 0;
-  list-style: none;
+  width: 100%;
+  margin-top: calc(var(--vertical-tabs-menu-separator-size) * -1);
+  content: "";
+  border-top: var(--vertical-tabs-menu-separator-size) solid var(--vertical-tabs-menu-separator-color);
 }
 
 .media-library-menu__link {
   position: relative;
   display: block;
-  box-sizing: border-box;
-  padding: 15px;
+  margin-top: calc(var(--vertical-tabs-border-size) * -1);
+  padding: var(--space-s) var(--space-s) var(--space-s) calc(var(--space-l) - var(--vertical-tabs-menu-link--active-border-size)); /* LTR */
   text-decoration: none;
-  border-bottom: 1px solid #b3b2ad;
-  background-color: #f2f2f0;
-  text-shadow: 0 1px hsla(0, 0%, 100%, 0.6);
+  word-wrap: break-word;
+  hyphens: auto;
+  color: var(--color-text);
+  border: var(--vertical-tabs-border-size) solid transparent;
+  border-width: var(--vertical-tabs-border-size) 0 var(--vertical-tabs-border-size) var(--vertical-tabs-menu-link--active-border-size); /* LTR */
+  border-radius: var(--vertical-tabs-border-radius) 0 0 var(--vertical-tabs-border-radius); /* LTR */
+}
+
+[dir="rtl"] .media-library-menu__link {
+  padding-right: calc(var(--space-l) - var(--vertical-tabs-menu-link--active-border-size));
+  padding-left: var(--space-s);
+  border-width: var(--vertical-tabs-border-size) var(--vertical-tabs-menu-link--active-border-size) var(--vertical-tabs-border-size) 0;
+  border-radius: 0 var(--vertical-tabs-border-radius) var(--vertical-tabs-border-radius) 0;
+}
+
+@media screen and (-ms-high-contrast: active) {
+  .media-library-menu__link {
+    border-color: transparent;
+  }
 }
 
-.media-library-menu__link:active,
-.media-library-menu__link:hover,
+/* Menu link states. */
 .media-library-menu__link:focus {
-  background: #fcfcfa;
-  text-shadow: none;
+  z-index: calc(var(--vertical-tabs-menu--z-index) + 3); /* Focus state should be on the highest level to make the focus effect be fully visible. This also means that it should have bigger z-index than the selected link. */
+  text-decoration: none;
+  box-shadow: none;
 }
 
-.media-library-menu__link:focus,
-.media-library-menu__link:active {
-  outline: none;
+.media-library-menu__link:hover {
+  text-decoration: none;
+  color: var(--color-absolutezero);
+  /* These borders are necessary to replace the dividing lines while in the hover state. */
+  border-top: var(--vertical-tabs-menu-separator-size) solid var(--vertical-tabs-menu-separator-color);
+  border-bottom: var(--vertical-tabs-menu-separator-size) solid var(--vertical-tabs-menu-separator-color);
+  background: var(--color-bgblue-hover);
+}
+
+/* This pseudo element provides the background for the hover state. */
+.media-library-menu__link::before {
+  position: absolute;
+  z-index: calc(var(--vertical-tabs-menu--z-index) - 1); /* This should be on a lower level than the menu-item separator lines. */
+  top: calc(var(--vertical-tabs-border-size) * -1);
+  right: 0; /* LTR */
+  bottom: calc(var(--vertical-tabs-border-size) * -1);
+  left: calc(var(--vertical-tabs-menu-link--active-border-size) * -1); /* LTR */
+  content: "";
+  pointer-events: none;
+  background-clip: padding-box;
+}
+[dir="rtl"] .media-library-menu__link::before {
+  right: calc(var(--vertical-tabs-menu-link--active-border-size) * -1);
+  left: 0;
+}
+
+.media-library-menu__link:focus::after {
+  position: absolute;
+  top: 0;
+  right: 0;
+  bottom: 0;
+  left: 0;
+  margin: calc(var(--vertical-tabs-border-size) * -1) calc(var(--vertical-tabs-menu-link--active-border-size) * -1);
+  content: "";
+  pointer-events: none;
+  border: var(--vertical-tabs-menu-link-focus-border-size) solid var(--color-focus);
+  border-radius: var(--vertical-tabs-border-radius);
 }
 
 .media-library-menu__link.active {
-  z-index: 1;
-  margin-right: -1px; /* LTR */
-  color: #000;
-  border-right: 1px solid #fcfcfa; /* LTR */
-  border-bottom: 1px solid #b3b2ad;
-  background-color: #fff;
-  box-shadow: 0 5px 5px -5px hsla(0, 0%, 0%, 0.3);
-}
-[dir="rtl"] .media-library-menu__link.active {
-  margin-right: 0;
-  margin-left: -1px;
-  border-right: 0;
-  border-left: 1px solid #fcfcfa;
+  z-index: calc(var(--vertical-tabs-menu--z-index) + 2); /* The selected menu link should be on a higher level than the white masking line that hides the grey separator. */
+  color: var(--color-absolutezero);
+  border-color: var(--vertical-tabs-border-color) transparent;
+  background-color: var(--color-white);
+  box-shadow: var(--vertical-tabs-shadow);
+}
+
+.media-library-menu__link.active:hover {
+  color: var(--color-absolutezero-hover);
+  background-color: var(--color-bgblue-hover);
+}
+
+.media-library-menu__link.active::before {
+  z-index: 1; /* The blue active-tab indication should be on a higher level than the green focus border. */
+  border-left: var(--vertical-tabs-menu-link--active-border-size) solid var(--vertical-tabs-menu-link--active-border-color); /* LTR */
+  border-radius: var(--base-border-radius) 0 0 var(--base-border-radius); /* LTR */
+}
+[dir=rtl] .media-library-menu__link.active::before {
+  border-right: var(--vertical-tabs-menu-link--active-border-size) solid var(--vertical-tabs-menu-link--active-border-color);
+  border-left: 0;
+  border-radius: 0 var(--base-border-radius) var(--base-border-radius) 0;
+}
+
+.media-library-menu__link.active:hover::before {
+  background: none;
 }
 
 .media-library-content {
   width: 100%;
   padding: 1em;
-  border-left: 1px solid #b3b2ad; /* LTR */
   outline: none;
 }
-[dir="rtl"] .media-library-content {
-  border-right: 1px solid #b3b2ad;
+
+.media-library-menu + .media-library-content {
+  z-index: var(--vertical-tabs-menu--z-index);
+  border-left: var(--vertical-tabs-border); /* LTR */
+  box-shadow: var(--vertical-tabs-shadow);
+}
+
+[dir="rtl"] .media-library-menu + .media-library-content {
+  border-right: var(--vertical-tabs-border);
   border-left: 0;
 }
 
 /* Generic media add form styles. */
 .media-library-add-form--without-input .form-item {
-  margin: 0 0 1em;
+  margin-right: 1rem;
 }
 
 /**
@@ -104,25 +199,62 @@
   outline: none;
 }
 
+/* This Media Library form is an exception to the extrasmall button pattern. */
+.media-library-add-form__added-media .media-library-add-form__remove-button.button--extrasmall {
+  margin: var(--space-xs) 0; /* LTR */
+  /* Left padding is double the background size of the button icon. */
+  padding: calc(calc(var(--space-xs) / 2) - 1px) calc(var(--space-s) - 1px) calc(calc(var(--space-xs) / 2) - 1px) calc(var(--space-s) * 2);
+}
+
+/* This is needed to override the default extrasmall button left margin. */
+[dir="rtl"] .media-library-add-form__added-media .media-library-add-form__remove-button.button--extrasmall {
+  margin-left: 0;
+}
+
 .media-library-add-form__input-wrapper {
-  padding: 16px;
-  border: 1px solid #bfbfbf;
-  border-radius: 2px;
-  background: #fcfcfa;
+  padding: var(--space-xs) var(--space-l) var(--space-l) var(--space-l);
+  border: var(--details-border-size) solid var(--details-border-color);
+  border-radius: var(--base-border-radius);
+  background-color: var(--color-white);
+  box-shadow: var(--details-box-shadow);
+  /* background: #fcfcfa; */
 }
 
 /* Style the media add upload form. */
 .media-library-add-form--upload.media-library-add-form--without-input .form-item-upload {
   margin-bottom: 0;
 }
+.media-library-add-form--upload.media-library-add-form--with-input .form-managed-file_meta {
+  margin-top: 0;
+}
+.media-library-add-form--upload.media-library-add-form--with-input .form-managed-file__main,
+.media-library-add-form--upload.media-library-add-form--with-input .form-managed-file.no-upload {
+  display: block;
+}
+
+/* Adjust the focus border on this element so it is not too close to buttons. */
+.media-library-add-form__added-media:focus {
+  box-shadow: 0 0 0 calc(var(--focus-border-offset-size) + 2px) var(--color-white), 0 0 0 calc(var(--focus-border-size) + var(--focus-border-offset-size) + 2px) var(--color-focus);
+}
 
 .media-library-add-form .file-upload-help {
   margin: 8px 0 0;
 }
 
+/* Align remove buttons with with Save button and compensate for IE scrollbar and focus padding. */
+@media all and (-ms-high-contrast: active), (-ms-high-contrast: none) {
+  .ui-dialog > .ui-dialog-content {
+    padding-right: calc(var(--space-s) - calc(var(--focus-border-size) + var(--focus-border-offset-size) + 2px));
+  }
+  [dir="rtl"] .ui-dialog > .ui-dialog-content {
+    padding-left: calc(var(--space-s) - calc(var(--focus-border-size) + var(--focus-border-offset-size) + 2px));
+  }
+}
+
 /* Style the media add oEmbed form. */
 .media-library-add-form--oembed .media-library-add-form__input-wrapper {
   display: flex;
+  align-items: center;
 }
 
 @media screen and (max-width: 37.5em) {
@@ -273,6 +405,37 @@
   position: relative;
 }
 
+/**
+ * Ajax throbbers inside a media library item.
+ */
+.media-library-item .ajax-progress.ajax-progress.ajax-progress {
+  position: absolute;
+  z-index: calc(var(--vertical-tabs-menu--z-index) + 1);
+  top: 50%;
+  left: 50%;
+  box-sizing: border-box;
+  width: 3rem; /* 56px */
+  height: 3rem;
+  margin: -1.5rem;
+  border: var(--input-border-size) solid var(--jui-dropdown-border-color);
+  border-radius: 3.5rem;
+  background: var(--color-white);
+  box-shadow: 0 0.25rem 0.625rem var(--jui-dropdown-shadow-color);
+}
+.media-library-item .ajax-progress__throbber {
+  position: absolute;
+  top: 50%;
+  left: 50%;
+  width: 1.75rem;
+  height: 1.75rem;
+  margin: -0.875rem;
+  border: 3px solid var(--color-absolutezero);
+  border-right: 3px dotted transparent;
+}
+.media-library-item .ajax-progress__message {
+  display: none;
+}
+
 /**
 * The media library item container receives screen reader focus when items are
 * removed. Since it is not an interactive element, it does not need an
@@ -288,6 +451,10 @@
   background: #fff;
 }
 
+.media-library-item--grid:focus {
+  box-shadow: none;
+}
+
 .media-library-item--grid:before {
   position: absolute;
   top: 7px;
@@ -298,6 +465,8 @@
   transition: border-color 0.2s, color 0.2s, background 0.2s;
   pointer-events: none;
   border: 1px solid #dbdbdb;
+  border-radius: 2px;
+  box-shadow: var(--details-box-shadow);
 }
 
 /* Media library widget weight field styles. */
@@ -396,12 +565,19 @@
   top: 5px;
   left: 5px;
   border-width: 3px;
-  border-color: #40b6ff;
   border-radius: 3px;
 }
+.media-library-item--grid.is-hover:before,
+.media-library-item--grid.checked.is-hover:before {
+  border-color: var(--color-absolutezero-hover);
+}
+
+.media-library-item--grid.is-focus:before {
+  border-color: var(--color-focus);
+}
 
 .media-library-item--grid.checked:before {
-  border-color: #0076c0;
+  border-color: var(--color-absolutezero);
 }
 
 .media-library-item__click-to-select-checkbox {
@@ -446,6 +622,11 @@
   cursor: move;
 }
 
+.field--widget-media-library-widget .media-library-item__preview img {
+  border-top-left-radius: 2px;
+  border-top-right-radius: 2px;
+}
+
 .field--widget-media-library-widget .js-media-library-item:only-child .media-library-item__preview {
   cursor: inherit;
 }
@@ -477,16 +658,13 @@
   background: white;
 }
 
-.media-library-item__name {
-  font-size: 14px;
-}
-
 .media-library-item__name {
   display: block;
   overflow: hidden;
-  margin: 2px;
+  margin: calc(var(--space-xs) / 2) var(--space-xs);
   white-space: nowrap;
   text-overflow: ellipsis;
+  font-size: 14px;
 }
 
 .media-library-item__attributes:hover .media-library-item__name,
@@ -523,14 +701,15 @@
   margin-left: 1em;
 }
 
-.media-library-widget__toggle-weight {
+.media-library-widget__toggle-weight.media-library-widget__toggle-weight {
   position: absolute;
-  top: 5px;
-  right: 5px; /* LTR */
+  top: var(--space-s);
+  right: var(--space-m); /* LTR */
+  text-decoration: none;
 }
-[dir="rtl"] .media-library-widget__toggle-weight {
+[dir="rtl"] .media-library-widget__toggle-weight.media-library-widget__toggle-weight {
   right: auto;
-  left: 5px;
+  left: var(--space-m);
 }
 
 /* Add negative margin for flex grid. */
@@ -560,15 +739,13 @@
   z-index: 1;
   top: 10px;
   overflow: hidden;
-  width: 21px;
-  height: 21px;
+  width: 24px;
+  height: 24px;
   margin: 5px;
   padding: 0;
   transition: 0.2s border-color;
   color: transparent;
-  border: 2px solid #ccc;
-  border-radius: 20px;
-  background-size: 13px;
+  background-size: 12px;
   text-shadow: none;
   font-size: 0;
 }
@@ -590,8 +767,15 @@
 }
 
 .media-library-item__edit {
-  background: url("../../../../misc/icons/787878/pencil.svg") #fff center no-repeat;
-  background-size: 13px;
+  /* !important to override button class border. */
+  border: 1px solid var(--color-lightgray) !important;
+  background-image: url("../../../../misc/icons/545560/pencil.svg");
+  background-repeat: no-repeat;
+  background-position: center;
+  background-size: 12px;
+}
+.media-library-item__edit:active {
+  background-image: url("../../../../misc/icons/ffffff/pencil.svg");
 }
 .media-library-item__remove,
 .media-library-item__remove.button,
@@ -600,17 +784,20 @@
 .media-library-item__remove.button:disabled:active,
 .media-library-item__remove.button:hover,
 .media-library-item__remove.button:focus {
-  background: url("../../../../misc/icons/787878/ex.svg") #fff center no-repeat;
-  background-size: 13px;
+  /* !important to override button class border. */
+  border: 1px solid var(--color-lightgray) !important;
+  background-image: url("../../../../misc/icons/545560/ex.svg");
+  background-repeat: no-repeat;
+  background-position: center;
+  background-size: 12px;
 }
-.media-library-item__edit:hover,
-.media-library-item__edit:focus,
-.media-library-item__remove:hover,
-.media-library-item__remove:focus,
-.media-library-item__remove.button:hover,
-.media-library-item__remove.button:focus,
+
+.media-library-item__remove:active,
+.media-library-item__remove.button:active,
 .media-library-item__remove.button:disabled:active {
-  border-color: #40b6ff;
+  /* !important to override button class border. */
+  border-color: var(--color-absolutezero) !important;
+  background-image: url("../../../../misc/icons/ffffff/ex.svg");
 }
 
 /**
@@ -623,26 +810,10 @@
 .media-library-add-form__media {
   position: relative;
   display: flex;
-  padding: 1em 0;
   border-bottom: 1px solid #c0c0c0;
   outline: none;
 }
 
-/* Do not show the top padding for the first item. */
-.media-library-add-form__media:first-child {
-  padding-top: 0;
-}
-
-/**
- * Change the position of the remove button for the first item.
- *
- * The first item doesn't have a top padding, change the location of the remove
- * button as well.
- */
-.media-library-add-form__media:first-child .media-library-add-form__remove-button[type="submit"] {
-  top: 5px;
-}
-
 /* Do not show the bottom border and padding for the last item. */
 .media-library-add-form__media:last-child {
   padding-bottom: 0;
@@ -655,7 +826,7 @@
   justify-content: center;
   width: 220px;
   margin-right: 20px; /* LTR */
-  background: #ebebeb;
+  background: var(--color-whitesmoke-o-40);
 }
 [dir="rtl"] .media-library-add-form__preview {
   margin-right: 0;
@@ -666,20 +837,17 @@
   flex-grow: 1;
 }
 
-/**
- * @todo Remove [type="submit"] when styles are moved to the seven theme in
- *   https://www.drupal.org/project/drupal/issues/2980769
- */
-.media-library-add-form__remove-button[type="submit"] {
+.media-library-add-form__remove-button {
   position: absolute;
-  top: 25px;
-  right: 6px;
-  margin-right: 0;
+  right: 0;
+  background-image: url("../../../../misc/icons/000000/ex.svg");
+  background-repeat: no-repeat;
+  background-position: var(--space-xs) center;
+  background-size: var(--space-s);
 }
-[dir="rtl"] .media-library-add-form__remove-button[type="submit"] {
+[dir="rtl"] .media-library-add-form__remove-button {
   right: auto;
-  left: 13px;
-  margin-left: 0;
+  left: 0;
 }
 
 /* @todo Remove in https://www.drupal.org/project/drupal/issues/3064914 */
diff --git a/core/themes/claro/src/ClaroPreRender.php b/core/themes/claro/src/ClaroPreRender.php
index d702543451..c8ec7db137 100644
--- a/core/themes/claro/src/ClaroPreRender.php
+++ b/core/themes/claro/src/ClaroPreRender.php
@@ -26,7 +26,7 @@ public static function managedFile($element) {
     }
 
     // Wrap single-cardinality widgets with a details element.
-    $single_file_widget = !empty($element['#cardinality']) && $element['#cardinality'] === 1;
+    $single_file_widget = empty($element['#do_not_wrap_in_details']) && !empty($element['#cardinality']) && $element['#cardinality'] === 1;
     if ($single_file_widget && empty($element['#single_wrapped'])) {
       $element['#theme_wrappers']['details'] = [
         '#title' => $element['#title'],