diff --git a/src/vs/workbench/parts/preferences/browser/media/settingsEditor2.css b/src/vs/workbench/parts/preferences/browser/media/settingsEditor2.css
index b40d4e59838522962d130160411ecc333b2eb1d4..b6ea2ae5985c7a56d4508d102ef6995abba25ff2 100644
--- a/src/vs/workbench/parts/preferences/browser/media/settingsEditor2.css
+++ b/src/vs/workbench/parts/preferences/browser/media/settingsEditor2.css
@@ -207,10 +207,34 @@
 	display: flex;
 }
 
+.settings-editor > .settings-body > .settings-tree-container .setting-item-bool > .reset-button-container {
+	margin-top: 5px;
+}
+
 .settings-editor > .settings-body > .settings-tree-container .setting-item-bool > .reset-button-container > .setting-reset-button {
 	width: initial;
 }
 
+.settings-editor > .settings-body > .settings-tree-container .setting-item-bool .setting-value-checkbox {
+	height: 16px;
+	width: 16px;
+	border: 1px solid transparent;
+	border-radius: 3px;
+	margin-right: 3px;
+	margin-left: 0px;
+	margin-top: 4px;
+	padding: 0px;
+	background-size: 14px !important;
+}
+
+.vs .settings-editor > .settings-body > .settings-tree-container .setting-item-bool .setting-value-checkbox.checked {
+	background: url('check.svg') center center no-repeat;
+}
+
+.vs-dark .settings-editor > .settings-body > .settings-tree-container .setting-item-bool .setting-value-checkbox.checked {
+	background: url('check-inverse.svg') center center no-repeat;
+}
+
 .settings-editor > .settings-body > .settings-tree-container .setting-item .setting-item-value {
 	margin-top: 7px;
 	display: flex;
diff --git a/src/vs/workbench/parts/preferences/browser/settingsEditor2.ts b/src/vs/workbench/parts/preferences/browser/settingsEditor2.ts
index 2515a7efbf311dd1077b19ca7d16b4d2be7e6dd0..17f5915836f7e2e80538d5222ef559af3e875868 100644
--- a/src/vs/workbench/parts/preferences/browser/settingsEditor2.ts
+++ b/src/vs/workbench/parts/preferences/browser/settingsEditor2.ts
@@ -513,7 +513,7 @@ export class SettingsEditor2 extends BaseEditor {
 			.then(() => {
 				if (focusedRowId) {
 					const rowSelector = `.setting-item#${focusedRowId}`;
-					const inputElementToFocus: HTMLElement = this.settingsTreeContainer.querySelector(`${rowSelector} input, ${rowSelector} select, ${rowSelector} a`);
+					const inputElementToFocus: HTMLElement = this.settingsTreeContainer.querySelector(`${rowSelector} input, ${rowSelector} select, ${rowSelector} a, ${rowSelector} .monaco-custom-checkbox`);
 					if (inputElementToFocus) {
 						inputElementToFocus.focus();
 						if (typeof selection === 'number') {
diff --git a/src/vs/workbench/parts/preferences/browser/settingsTree.ts b/src/vs/workbench/parts/preferences/browser/settingsTree.ts
index be329d4e82cf064d6e644ff0ede6d28b2e1873e3..71311d1e7c92aa0648dc24e64d06bee0b670fd46 100644
--- a/src/vs/workbench/parts/preferences/browser/settingsTree.ts
+++ b/src/vs/workbench/parts/preferences/browser/settingsTree.ts
@@ -7,6 +7,7 @@ import * as DOM from 'vs/base/browser/dom';
 import { StandardKeyboardEvent } from 'vs/base/browser/keyboardEvent';
 import { IMouseEvent } from 'vs/base/browser/mouseEvent';
 import { Button } from 'vs/base/browser/ui/button/button';
+import { Checkbox } from 'vs/base/browser/ui/checkbox/checkbox';
 import { InputBox } from 'vs/base/browser/ui/inputbox/inputBox';
 import { SelectBox } from 'vs/base/browser/ui/selectBox/selectBox';
 import * as arrays from 'vs/base/common/arrays';
@@ -22,8 +23,8 @@ import { IAccessibilityProvider, IDataSource, IFilter, IRenderer, ITree } from '
 import { localize } from 'vs/nls';
 import { ConfigurationTarget, IConfigurationService } from 'vs/platform/configuration/common/configuration';
 import { IContextViewService } from 'vs/platform/contextview/browser/contextView';
-import { WorkbenchTreeController, WorkbenchTree } from 'vs/platform/list/browser/listService';
-import { editorActiveLinkForeground, registerColor } from 'vs/platform/theme/common/colorRegistry';
+import { WorkbenchTree, WorkbenchTreeController } from 'vs/platform/list/browser/listService';
+import { editorActiveLinkForeground, editorBackground, inputBackground, registerColor, selectBorder } from 'vs/platform/theme/common/colorRegistry';
 import { attachButtonStyler, attachInputBoxStyler, attachSelectBoxStyler } from 'vs/platform/theme/common/styler';
 import { ICssStyleCollector, ITheme, IThemeService, registerThemingParticipant } from 'vs/platform/theme/common/themeService';
 import { SettingsTarget } from 'vs/workbench/parts/preferences/browser/preferencesWidgets';
@@ -45,6 +46,20 @@ registerThemingParticipant((theme: ITheme, collector: ICssStyleCollector) => {
 	}
 });
 
+registerThemingParticipant((theme: ITheme, collector: ICssStyleCollector) => {
+	const inputBackgroundColor = theme.getColor(inputBackground);
+	const selectBorderColor = theme.getColor(selectBorder);
+	const editorBackgroundColor = theme.getColor(editorBackground);
+
+	if (inputBackgroundColor) {
+		collector.addRule(`.settings-editor > .settings-body > .settings-tree-container .setting-item-bool .setting-value-checkbox { background-color: ${inputBackgroundColor} !important; }`);
+	}
+
+	if (selectBorderColor && (editorBackgroundColor.equals(inputBackgroundColor))) {
+		collector.addRule(`.settings-editor > .settings-body > .settings-tree-container .setting-item-bool .setting-value-checkbox { border-color: ${selectBorderColor} !important; }`);
+	}
+});
+
 export abstract class SettingsTreeElement {
 	id: string;
 	parent: any; // SearchResultModel or group element... TODO search should be more similar to the normal case
@@ -684,12 +699,15 @@ export class SettingsRenderer implements IRenderer {
 	}
 
 	private renderBool(dataElement: SettingsTreeSettingElement, isSelected: boolean, template: ISettingBoolItemTemplate, element: HTMLElement, onChange: (value: boolean) => void): void {
-		const checkboxElement = <HTMLInputElement>DOM.append(element, $('input.setting-value-checkbox.setting-value-input'));
-		checkboxElement.type = 'checkbox';
-		checkboxElement.checked = dataElement.value;
-		checkboxElement.tabIndex = isSelected ? 0 : -1;
+		const checkbox = new Checkbox({ actionClassName: 'setting-value-checkbox', isChecked: dataElement.value, title: '', inputActiveOptionBorder: null });
+		template.toDispose.push(checkbox);
+
+		template.toDispose.push(checkbox.onChange(() => {
+			onChange(checkbox.checked);
+		}));
 
-		template.toDispose.push(DOM.addDisposableListener(checkboxElement, 'change', e => onChange(checkboxElement.checked)));
+		element.appendChild(checkbox.domNode);
+		checkbox.domNode.tabIndex = isSelected ? 0 : -1;
 	}
 
 	private renderEnum(dataElement: SettingsTreeSettingElement, isSelected: boolean, template: ISettingItemTemplate, element: HTMLElement, onChange: (value: string) => void): void {