diff --git a/packages/calcite-components/src/components/dropdown-item/dropdown-item.scss b/packages/calcite-components/src/components/dropdown-item/dropdown-item.scss
index 41490aa455c..2a7011ced55 100644
--- a/packages/calcite-components/src/components/dropdown-item/dropdown-item.scss
+++ b/packages/calcite-components/src/components/dropdown-item/dropdown-item.scss
@@ -34,11 +34,7 @@
 
 // item icon
 .dropdown-item-icon {
-  @apply relative
-    opacity-0
-    duration-150
-    ease-in-out;
-  transform: scale(0.9);
+  @apply relative;
 }
 
 :host([scale="s"]) {
@@ -120,12 +116,10 @@
 
 :host(:hover:not([disabled])) .dropdown-item-icon {
   color: theme("borderColor.color.1");
-  @apply opacity-100;
 }
 
 :host([selected]) .dropdown-item-icon {
   color: theme("backgroundColor.brand");
-  @apply opacity-100;
 }
 
 @include base-component();
diff --git a/packages/calcite-components/src/components/dropdown-item/dropdown-item.tsx b/packages/calcite-components/src/components/dropdown-item/dropdown-item.tsx
index 2c68f75ed6c..4a108aa989e 100644
--- a/packages/calcite-components/src/components/dropdown-item/dropdown-item.tsx
+++ b/packages/calcite-components/src/components/dropdown-item/dropdown-item.tsx
@@ -7,6 +7,7 @@ import {
   method,
   JsxNode,
   setAttribute,
+  state,
 } from "@arcgis/lumina";
 import { toAriaBoolean } from "../../utils/dom";
 import { ItemKeyboardEvent } from "../dropdown/interfaces";
@@ -24,7 +25,7 @@ import {
   InteractiveContainer,
   updateHostInteraction,
 } from "../../utils/interactive";
-import { IconNameOrString } from "../icon/interfaces";
+import { IconName, IconNameOrString } from "../icon/interfaces";
 import type { DropdownGroup } from "../dropdown-group/dropdown-group";
 import { CSS } from "./resources";
 import { styles } from "./dropdown-item.scss";
@@ -48,6 +49,8 @@ export class DropdownItem extends LitElement implements InteractiveComponent, Lo
   /** if href is requested, track the rendered child link */
   private childLink = createRef<HTMLAnchorElement>();
 
+  @state() hovered = false;
+
   /** id of containing group */
   private parentDropdownGroupEl: DropdownGroup["el"];
 
@@ -145,6 +148,8 @@ export class DropdownItem extends LitElement implements InteractiveComponent, Lo
     super();
     this.listen("click", this.onClick);
     this.listen("keydown", this.keyDownHandler);
+    this.listen("pointerover", this.handlePointerOver);
+    this.listen("pointerout", this.handlePointerOut);
     this.listenOn<CustomEvent>(
       document.body,
       "calciteInternalDropdownItemChange",
@@ -173,6 +178,14 @@ export class DropdownItem extends LitElement implements InteractiveComponent, Lo
 
   // #region Private Methods
 
+  private handlePointerOver(): void {
+    this.hovered = true;
+  }
+
+  private handlePointerOut(): void {
+    this.hovered = false;
+  }
+
   private onClick(): void {
     this.emitRequestedItem();
   }
@@ -333,18 +346,35 @@ export class DropdownItem extends LitElement implements InteractiveComponent, Lo
             [CSS.containerNone]: selectionMode === "none",
           }}
         >
-          {selectionMode !== "none" ? (
-            <calcite-icon
-              class={CSS.icon}
-              icon={selectionMode === "multiple" ? "check" : "bullet-point"}
-              scale={getIconScale(this.scale)}
-            />
-          ) : null}
+          {this.renderSelectionIcon()}
           {contentEl}
         </div>
       </InteractiveContainer>
     );
   }
 
+  private renderSelectionIcon(): JsxNode {
+    const { hovered, selected, selectionMode, scale } = this;
+
+    if (selectionMode === "none") {
+      return null;
+    }
+
+    const icon: IconName =
+      selectionMode === "multiple"
+        ? selected
+          ? "check-square-f"
+          : hovered
+            ? "check-square"
+            : "square"
+        : selected || hovered
+          ? scale === "l"
+            ? "bullet-point-large"
+            : "bullet-point"
+          : "blank";
+
+    return <calcite-icon class={CSS.icon} icon={icon} scale={getIconScale(scale)} />;
+  }
+
   // #endregion
 }