diff --git a/apps/client/src/widgets/react/Icon.tsx b/apps/client/src/widgets/react/Icon.tsx
index e047a1762..6d17dc3b9 100644
--- a/apps/client/src/widgets/react/Icon.tsx
+++ b/apps/client/src/widgets/react/Icon.tsx
@@ -1,8 +1,16 @@
-interface IconProps {
+import clsx from "clsx";
+import { HTMLAttributes } from "preact";
+
+interface IconProps extends Pick<HTMLAttributes<HTMLSpanElement>, "className" | "onClick"> {
     icon?: string;
     className?: string;
 }
 
-export default function Icon({ icon, className }: IconProps) {
-    return <span class={`${icon ?? "bx bx-empty"} ${className ?? ""}`}></span>
-}
\ No newline at end of file
+export default function Icon({ icon, className, ...restProps }: IconProps) {
+    return (
+        <span
+            class={clsx(icon ?? "bx bx-empty", className)}
+            {...restProps}
+        />
+    );
+}
diff --git a/apps/client/src/widgets/sidebar/TableOfContents.css b/apps/client/src/widgets/sidebar/TableOfContents.css
new file mode 100644
index 000000000..79c6ee548
--- /dev/null
+++ b/apps/client/src/widgets/sidebar/TableOfContents.css
@@ -0,0 +1,82 @@
+.toc ol {
+    position: relative;
+    overflow: hidden;
+    padding-inline-start: 0px;
+    transition: max-height 0.3s ease;
+}
+
+.toc li.collapsed + ol {
+    display:none;
+}
+
+.toc li + ol:before {
+    content: "";
+    position: absolute;
+    height: 100%;
+    border-inline-start: 1px solid var(--main-border-color);
+    z-index: 10;
+}
+
+.toc li {
+    display: flex;
+    position: relative;
+    list-style: none;
+    align-items: center;
+    padding-inline-start: 7px;
+    cursor: pointer;
+    text-align: justify;
+    word-wrap: break-word;
+    hyphens: auto;
+}
+
+.toc > ol {
+    --toc-depth-level: 1;
+}
+.toc > ol > ol {
+    --toc-depth-level: 2;
+}
+.toc > ol > ol > ol {
+    --toc-depth-level: 3;
+}
+.toc > ol > ol > ol > ol {
+    --toc-depth-level: 4;
+}
+.toc > ol > ol > ol > ol > ol {
+    --toc-depth-level: 5;
+}
+
+.toc > ol ol::before {
+    inset-inline-start: calc((var(--toc-depth-level) - 2) * 20px + 14px);
+}
+
+.toc li {
+    padding-inline-start: calc((var(--toc-depth-level) - 1) * 20px + 4px);
+}
+
+.toc li .collapse-button {
+    display: flex;
+    position: relative;
+    width: 21px;
+    height: 21px;
+    flex-shrink: 0;
+    align-items: center;
+    justify-content: center;
+    transition: transform 0.3s ease;
+}
+
+.toc li.collapsed .collapse-button {
+    transform: rotate(-90deg);
+}
+
+.toc li .item-content {
+    margin-inline-start: 25px;
+    flex: 1;
+}
+
+.toc li .collapse-button + .item-content {
+    margin-inline-start: 4px;
+}
+
+.toc li:hover {
+    font-weight: bold;
+}
diff --git a/apps/client/src/widgets/sidebar/TableOfContents.tsx b/apps/client/src/widgets/sidebar/TableOfContents.tsx
index b4391b678..8ed728c26 100644
--- a/apps/client/src/widgets/sidebar/TableOfContents.tsx
+++ b/apps/client/src/widgets/sidebar/TableOfContents.tsx
@@ -1,8 +1,12 @@
+import "./TableOfContents.css";
+
 import { CKTextEditor, ModelElement } from "@triliumnext/ckeditor5";
+import clsx from "clsx";
 import { useEffect, useState } from "preact/hooks";
 
 import { t } from "../../services/i18n";
 import { useActiveNoteContext, useIsNoteReadOnly, useNoteProperty, useTextEditor } from "../react/hooks";
+import Icon from "../react/Icon";
 import RightPanelWidget from "./RightPanelWidget";
 
 interface RawHeading {
@@ -66,19 +70,35 @@ function AbstractTableOfContents({ headings }: {
     headings: RawHeading[];
 }) {
     const nestedHeadings = buildHeadingTree(headings);
-    return nestedHeadings.map(heading => <TableOfContentsHeading heading={heading} />);
+    return (
+        <span className="toc">
+            <ol>
+                {nestedHeadings.map(heading => <TableOfContentsHeading heading={heading} />)}
+            </ol>
+        </span>
+    );
 }
 
 function TableOfContentsHeading({ heading }: { heading: HeadingsWithNesting }) {
+    const [ collapsed, setCollapsed ] = useState(false);
     return (
-        <li>
-            <span className="title">{heading.text}</span>
+        <>
+            <li className={clsx(collapsed && "collapsed")}>
+                {heading.children.length > 0 && (
+                    <Icon
+                        className="collapse-button"
+                        icon="bx bx-chevron-down"
+                        onClick={() => setCollapsed(!collapsed)}
+                    />
+                )}
+                <span className="item-content">{heading.text}</span>
+            </li>
             {heading.children && (
-                <ul>
+                <ol>
                     {heading.children.map(heading => <TableOfContentsHeading heading={heading} />)}
-                </ul>
+                </ol>
             )}
-        </li>
+        </>
     );
 }