diff --git a/packages/@lwc/engine-core/src/framework/renderer.ts b/packages/@lwc/engine-core/src/framework/renderer.ts
index 851098b84a..a9ea488791 100644
--- a/packages/@lwc/engine-core/src/framework/renderer.ts
+++ b/packages/@lwc/engine-core/src/framework/renderer.ts
@@ -46,6 +46,7 @@ export interface Renderer<N = HostNode, E = HostElement> {
     getElementsByClassName(element: E, names: string): HTMLCollection;
     isConnected(node: N): boolean;
     insertGlobalStylesheet(content: string): void;
+    insertStylesheet(content: string, target: N): void;
     assertInstanceOfHTMLElement?(elm: any, msg: string): void;
     defineCustomElement(
         name: string,
diff --git a/packages/@lwc/engine-core/src/framework/stylesheet.ts b/packages/@lwc/engine-core/src/framework/stylesheet.ts
index 3e6d7ca68a..1c8af5028f 100644
--- a/packages/@lwc/engine-core/src/framework/stylesheet.ts
+++ b/packages/@lwc/engine-core/src/framework/stylesheet.ts
@@ -4,7 +4,7 @@
  * SPDX-License-Identifier: MIT
  * For full license text, see the LICENSE file in the repo root or https://opensource.org/licenses/MIT
  */
-import { isArray, isUndefined, ArrayJoin, ArrayPush } from '@lwc/shared';
+import { isArray, isUndefined, ArrayJoin, ArrayPush, isNull } from '@lwc/shared';
 
 import * as api from './api';
 import { VNode } from '../3rdparty/snabbdom/types';
@@ -138,16 +138,42 @@ export function getStylesheetsContent(vm: VM, template: Template): string[] {
     return content;
 }
 
+// It might be worth caching this to avoid doing the lookup repeatedly, but
+// perf testing has not shown it to be a huge improvement yet:
+// https://github.com/salesforce/lwc/pull/2460#discussion_r691208892
+function getNearestNativeShadowComponent(vm: VM): VM | null {
+    let owner: VM | null = vm;
+    while (!isNull(owner)) {
+        if (owner.renderMode === RenderMode.Shadow && owner.shadowMode === ShadowMode.Native) {
+            return owner;
+        }
+        owner = owner.owner;
+    }
+    return owner;
+}
+
 export function createStylesheet(vm: VM, stylesheets: string[]): VNode | null {
     const { renderer, renderMode, shadowMode } = vm;
     if (renderMode === RenderMode.Shadow && shadowMode === ShadowMode.Synthetic) {
         for (let i = 0; i < stylesheets.length; i++) {
             renderer.insertGlobalStylesheet(stylesheets[i]);
         }
-        return null;
-    } else {
-        // native shadow or light DOM
+    } else if (renderer.ssr) {
+        // native shadow or light DOM, SSR
         const combinedStylesheetContent = ArrayJoin.call(stylesheets, '\n');
         return createInlineStyleVNode(combinedStylesheetContent);
+    } else {
+        // native shadow or light DOM, DOM renderer
+        const root = getNearestNativeShadowComponent(vm);
+        const isGlobal = isNull(root);
+        for (let i = 0; i < stylesheets.length; i++) {
+            if (isGlobal) {
+                renderer.insertGlobalStylesheet(stylesheets[i]);
+            } else {
+                // local level
+                renderer.insertStylesheet(stylesheets[i], root!.cmpRoot);
+            }
+        }
     }
+    return null;
 }
diff --git a/packages/@lwc/engine-dom/src/renderer.ts b/packages/@lwc/engine-dom/src/renderer.ts
index 38ac201530..25757dfe84 100644
--- a/packages/@lwc/engine-dom/src/renderer.ts
+++ b/packages/@lwc/engine-dom/src/renderer.ts
@@ -10,6 +10,7 @@ import {
     create,
     hasOwnProperty,
     htmlPropertyToAttribute,
+    isFunction,
     isUndefined,
     KEY__SHADOW_TOKEN,
     setPrototypeOf,
@@ -29,6 +30,10 @@ if (process.env.NODE_ENV === 'development') {
 }
 
 const globalStylesheetsParentElement: Element = document.head || document.body || document;
+const supportsConstructableStyleSheets = isFunction((CSSStyleSheet.prototype as any).replaceSync);
+const styleElements: { [content: string]: HTMLStyleElement } = create(null);
+const styleSheets: { [content: string]: CSSStyleSheet } = create(null);
+const nodesToStyleSheets = new WeakMap<Node, { [content: string]: true }>();
 
 let getCustomElement, defineCustomElement, HTMLElementConstructor;
 
@@ -54,6 +59,46 @@ function isCustomElementRegistryAvailable() {
     }
 }
 
+function insertConstructableStyleSheet(content: string, target: Node) {
+    // It's important for CSSStyleSheets to be unique based on their content, so that
+    // `shadowRoot.adoptedStyleSheets.includes(sheet)` works.
+    let styleSheet = styleSheets[content];
+    if (isUndefined(styleSheet)) {
+        styleSheet = new CSSStyleSheet();
+        (styleSheet as any).replaceSync(content);
+        styleSheets[content] = styleSheet;
+    }
+    if (!(target as any).adoptedStyleSheets.includes(styleSheet)) {
+        (target as any).adoptedStyleSheets = [...(target as any).adoptedStyleSheets, styleSheet];
+    }
+}
+
+function insertStyleElement(content: string, target: Node) {
+    // Avoid inserting duplicate `<style>`s
+    let sheets = nodesToStyleSheets.get(target);
+    if (isUndefined(sheets)) {
+        sheets = create(null);
+        nodesToStyleSheets.set(target, sheets!);
+    }
+    if (sheets![content]) {
+        return;
+    }
+    sheets![content] = true;
+
+    // This `<style>` may be repeated multiple times in the DOM, so cache it. It's a bit
+    // faster to call `cloneNode()` on an existing node than to recreate it every time.
+    let elm = styleElements[content];
+    if (isUndefined(elm)) {
+        elm = document.createElement('style');
+        elm.type = 'text/css';
+        elm.textContent = content;
+        styleElements[content] = elm;
+    } else {
+        elm = elm.cloneNode(true) as HTMLStyleElement;
+    }
+    target.appendChild(elm);
+}
+
 if (isCustomElementRegistryAvailable()) {
     getCustomElement = customElements.get.bind(customElements);
     defineCustomElement = customElements.define.bind(customElements);
@@ -244,6 +289,15 @@ export const renderer: Renderer<Node, Element> = {
         globalStylesheetsParentElement.appendChild(elm);
     },
 
+    insertStylesheet(content: string, target: Node): void {
+        if (supportsConstructableStyleSheets) {
+            insertConstructableStyleSheet(content, target);
+        } else {
+            // Fall back to <style> element
+            insertStyleElement(content, target);
+        }
+    },
+
     assertInstanceOfHTMLElement(elm: any, msg: string) {
         assert.invariant(elm instanceof HTMLElement, msg);
     },
diff --git a/packages/@lwc/engine-server/src/renderer.ts b/packages/@lwc/engine-server/src/renderer.ts
index 8e4202eabd..3fa98f96ff 100644
--- a/packages/@lwc/engine-server/src/renderer.ts
+++ b/packages/@lwc/engine-server/src/renderer.ts
@@ -299,6 +299,11 @@ export const renderer: Renderer<HostNode, HostElement> = {
         // synthetic shadow.
     },
 
+    insertStylesheet() {
+        // Noop on SSR (for now). This need to be reevaluated whenever we will implement support for
+        // synthetic shadow.
+    },
+
     addEventListener() {
         // Noop on SSR.
     },
diff --git a/packages/integration-karma/test/light-dom/multiple-templates/index.spec.js b/packages/integration-karma/test/light-dom/multiple-templates/index.spec.js
index fb30c13362..0f4f5ef2e9 100644
--- a/packages/integration-karma/test/light-dom/multiple-templates/index.spec.js
+++ b/packages/integration-karma/test/light-dom/multiple-templates/index.spec.js
@@ -23,7 +23,9 @@ describe('multiple templates', () => {
         element.next();
         return Promise.resolve().then(() => {
             expect(element.querySelector('div').textContent).toEqual('b');
-            expect(getComputedStyle(element.querySelector('div')).color).toEqual('rgb(0, 0, 0)');
+            expect(getComputedStyle(element.querySelector('div')).color).toEqual(
+                'rgb(233, 150, 122)'
+            );
             expect(getComputedStyle(element.querySelector('div')).marginLeft).toEqual('10px');
             // element should not be dirty after template change
             expect(element.querySelector('div').hasAttribute('foo')).toEqual(false);
diff --git a/packages/integration-karma/test/rendering/elements-are-not-recycled/index.spec.js b/packages/integration-karma/test/rendering/elements-are-not-recycled/index.spec.js
index 71a74f451a..bfb1b9059f 100644
--- a/packages/integration-karma/test/rendering/elements-are-not-recycled/index.spec.js
+++ b/packages/integration-karma/test/rendering/elements-are-not-recycled/index.spec.js
@@ -101,8 +101,14 @@ if (process.env.NATIVE_SHADOW) {
         document.body.appendChild(elm);
 
         return Promise.resolve().then(() => {
-            const styles = Array.from(elm.shadowRoot.querySelectorAll('x-simple')).map((xSimple) =>
-                xSimple.shadowRoot.querySelector('style')
+            const styles = Array.from(elm.shadowRoot.querySelectorAll('x-simple')).map(
+                (xSimple) => {
+                    // if constructable stylesheets are supported, return that rather than <style> tags
+                    return (
+                        xSimple.shadowRoot.adoptedStyleSheets ||
+                        xSimple.shadowRoot.querySelector('style')
+                    );
+                }
             );
 
             expect(styles[0]).toBeTruthy();
diff --git a/packages/integration-karma/test/shadow-dom/multiple-templates/index.spec.js b/packages/integration-karma/test/shadow-dom/multiple-templates/index.spec.js
new file mode 100644
index 0000000000..2cab5ba852
--- /dev/null
+++ b/packages/integration-karma/test/shadow-dom/multiple-templates/index.spec.js
@@ -0,0 +1,41 @@
+import { createElement } from 'lwc';
+import Multi from 'x/multi';
+
+if (process.env.NATIVE_SHADOW) {
+    describe('Shadow DOM styling - multiple shadow DOM components', () => {
+        it('Does not duplicate styles if template is re-rendered', () => {
+            const element = createElement('x-multi', { is: Multi });
+
+            const getNumStyleSheets = () => {
+                if (element.shadowRoot.adoptedStyleSheets) {
+                    return element.shadowRoot.adoptedStyleSheets.length;
+                } else {
+                    return element.shadowRoot.querySelectorAll('style').length;
+                }
+            };
+
+            document.body.appendChild(element);
+            return Promise.resolve()
+                .then(() => {
+                    expect(getComputedStyle(element.shadowRoot.querySelector('div')).color).toEqual(
+                        'rgb(0, 0, 255)'
+                    );
+                    expect(getNumStyleSheets()).toEqual(1);
+                    element.next();
+                })
+                .then(() => {
+                    expect(getComputedStyle(element.shadowRoot.querySelector('div')).color).toEqual(
+                        'rgb(255, 0, 0)'
+                    );
+                    expect(getNumStyleSheets()).toEqual(2);
+                    element.next();
+                })
+                .then(() => {
+                    expect(getComputedStyle(element.shadowRoot.querySelector('div')).color).toEqual(
+                        'rgb(0, 0, 255)'
+                    );
+                    expect(getNumStyleSheets()).toEqual(2);
+                });
+        });
+    });
+}
diff --git a/packages/integration-karma/test/shadow-dom/multiple-templates/x/multi/a.css b/packages/integration-karma/test/shadow-dom/multiple-templates/x/multi/a.css
new file mode 100644
index 0000000000..91b0d5daea
--- /dev/null
+++ b/packages/integration-karma/test/shadow-dom/multiple-templates/x/multi/a.css
@@ -0,0 +1,3 @@
+.blue {
+    color: blue;
+}
diff --git a/packages/integration-karma/test/shadow-dom/multiple-templates/x/multi/a.html b/packages/integration-karma/test/shadow-dom/multiple-templates/x/multi/a.html
new file mode 100644
index 0000000000..60f71823f3
--- /dev/null
+++ b/packages/integration-karma/test/shadow-dom/multiple-templates/x/multi/a.html
@@ -0,0 +1,3 @@
+<template>
+  <div class="blue">a</div>
+</template>
diff --git a/packages/integration-karma/test/shadow-dom/multiple-templates/x/multi/b.css b/packages/integration-karma/test/shadow-dom/multiple-templates/x/multi/b.css
new file mode 100644
index 0000000000..75424513d6
--- /dev/null
+++ b/packages/integration-karma/test/shadow-dom/multiple-templates/x/multi/b.css
@@ -0,0 +1,3 @@
+.red {
+    color: red;
+}
diff --git a/packages/integration-karma/test/shadow-dom/multiple-templates/x/multi/b.html b/packages/integration-karma/test/shadow-dom/multiple-templates/x/multi/b.html
new file mode 100644
index 0000000000..9663e6a2ed
--- /dev/null
+++ b/packages/integration-karma/test/shadow-dom/multiple-templates/x/multi/b.html
@@ -0,0 +1,3 @@
+<template>
+  <div class="red">b</div>
+</template>
diff --git a/packages/integration-karma/test/shadow-dom/multiple-templates/x/multi/multi.js b/packages/integration-karma/test/shadow-dom/multiple-templates/x/multi/multi.js
new file mode 100644
index 0000000000..6e524c36b9
--- /dev/null
+++ b/packages/integration-karma/test/shadow-dom/multiple-templates/x/multi/multi.js
@@ -0,0 +1,16 @@
+import { LightningElement, api } from 'lwc';
+import A from './a.html';
+import B from './b.html';
+
+export default class Multi extends LightningElement {
+    current = A;
+
+    @api
+    next() {
+        this.current = this.current === A ? B : A;
+    }
+
+    render() {
+        return this.current;
+    }
+}
diff --git a/packages/perf-benchmarks-components/rollup.config.js b/packages/perf-benchmarks-components/rollup.config.js
index eacdf680ff..8e1f386950 100644
--- a/packages/perf-benchmarks-components/rollup.config.js
+++ b/packages/perf-benchmarks-components/rollup.config.js
@@ -9,10 +9,14 @@ import path from 'path';
 import glob from 'glob';
 import lwc from '@lwc/rollup-plugin';
 import replace from '@rollup/plugin-replace';
+import { generateStyledComponents } from './scripts/generate-styled-components';
 
-const rootDir = path.join(__dirname, 'src');
+const { tmpDir, styledComponents } = generateStyledComponents();
 
 function createConfig(componentFile, engineType) {
+    const rootDir = componentFile.includes(tmpDir)
+        ? path.join(tmpDir, 'src')
+        : path.join(__dirname, 'src');
     const lwcImportModule = engineType === 'server' ? '@lwc/engine-server' : '@lwc/engine-dom';
     return {
         input: componentFile,
@@ -34,7 +38,7 @@ function createConfig(componentFile, engineType) {
             }),
         ],
         output: {
-            file: componentFile.replace('/src/', `/dist/${engineType}/`),
+            file: componentFile.replace(tmpDir, __dirname).replace('/src/', `/dist/${engineType}/`),
             format: 'esm',
         },
         // These packages need to be external so that perf-benchmarks can potentially swap them out
@@ -43,7 +47,7 @@ function createConfig(componentFile, engineType) {
     };
 }
 
-const components = glob.sync(path.join(__dirname, 'src/**/*.js'));
+const components = [...glob.sync(path.join(__dirname, 'src/**/*.js')), ...styledComponents];
 
 const config = ['server', 'dom']
     .map((engineType) => components.map((component) => createConfig(component, engineType)))
diff --git a/packages/perf-benchmarks-components/scripts/generate-styled-components.js b/packages/perf-benchmarks-components/scripts/generate-styled-components.js
new file mode 100644
index 0000000000..24cf213aff
--- /dev/null
+++ b/packages/perf-benchmarks-components/scripts/generate-styled-components.js
@@ -0,0 +1,55 @@
+/*
+ * Copyright (c) 2018, salesforce.com, inc.
+ * All rights reserved.
+ * SPDX-License-Identifier: MIT
+ * For full license text, see the LICENSE file in the repo root or https://opensource.org/licenses/MIT
+ */
+
+import path from 'path';
+import fs from 'fs';
+import os from 'os';
+
+const NUM_COMPONENTS = 1000;
+
+// Generates some components with individual CSS for each one.
+// We could use @rollup/plugin-virtual for this, but @lwc/rollup-plugin deliberately
+// filters virtual modules, so it's simpler to just write to a temp dir.
+export function generateStyledComponents() {
+    const tmpDir = fs.mkdtempSync(path.join(os.tmpdir(), 'lwc-'));
+
+    const components = Array(NUM_COMPONENTS)
+        .fill()
+        .map((_, i) =>
+            path.join(tmpDir, `src/benchmark/styledComponent${i}/styledComponent${i}.js`)
+        );
+
+    components.forEach((jsFilename, i) => {
+        const cssFilename = jsFilename.replace('.js', '.css');
+        const htmlFilename = jsFilename.replace('.js', '.html');
+
+        const js =
+            'import { LightningElement } from "lwc"; export default class extends LightningElement {}';
+        const css = `div { color: ${i.toString(16).padStart(6, '0')}}`;
+        const html = '<template><div></div></template>';
+
+        fs.mkdirSync(path.dirname(jsFilename), { recursive: true });
+        fs.writeFileSync(jsFilename, js, 'utf-8');
+        fs.writeFileSync(cssFilename, css, 'utf-8');
+        fs.writeFileSync(htmlFilename, html, 'utf-8');
+    });
+
+    const oneComponentFilename = path.join(tmpDir, 'src/benchmark/styledComponent.js');
+    const oneComponent = `export { default } from ${JSON.stringify(components[0])};`;
+    fs.writeFileSync(oneComponentFilename, oneComponent, 'utf-8');
+
+    const allComponentsFilename = path.join(tmpDir, 'src/benchmark/styledComponents.js');
+    const allComponents = `
+        ${components.map((mod, i) => `import cmp${i} from ${JSON.stringify(mod)}`).join(';')};
+        export default [${components.map((_, i) => `cmp${i}`).join(',')}];`;
+    fs.writeFileSync(allComponentsFilename, allComponents, 'utf-8');
+
+    return {
+        styledComponents: [oneComponentFilename, allComponentsFilename],
+        tmpDir,
+    };
+}
diff --git a/packages/perf-benchmarks/src/__benchmarks__/engine-dom/benchmark-styled-component/ss-styled-component-create-1k-different.benchmark.js b/packages/perf-benchmarks/src/__benchmarks__/engine-dom/benchmark-styled-component/ss-styled-component-create-1k-different.benchmark.js
new file mode 100644
index 0000000000..44fed4c135
--- /dev/null
+++ b/packages/perf-benchmarks/src/__benchmarks__/engine-dom/benchmark-styled-component/ss-styled-component-create-1k-different.benchmark.js
@@ -0,0 +1,12 @@
+/*
+ * Copyright (c) 2018, salesforce.com, inc.
+ * All rights reserved.
+ * SPDX-License-Identifier: MIT
+ * For full license text, see the LICENSE file in the repo root or https://opensource.org/licenses/MIT
+ */
+
+import components from 'perf-benchmarks-components/dist/dom/benchmark/styledComponents.js';
+import { styledComponentBenchmark } from '../../../utils/styledComponentBenchmark';
+
+// Create 1k components with different CSS in each component
+styledComponentBenchmark(`ss-benchmark-styled-component/create/1k/different`, components);
diff --git a/packages/perf-benchmarks/src/__benchmarks__/engine-dom/benchmark-styled-component/ss-styled-component-create-1k-same.benchmark.js b/packages/perf-benchmarks/src/__benchmarks__/engine-dom/benchmark-styled-component/ss-styled-component-create-1k-same.benchmark.js
new file mode 100644
index 0000000000..b784a466d5
--- /dev/null
+++ b/packages/perf-benchmarks/src/__benchmarks__/engine-dom/benchmark-styled-component/ss-styled-component-create-1k-same.benchmark.js
@@ -0,0 +1,12 @@
+/*
+ * Copyright (c) 2018, salesforce.com, inc.
+ * All rights reserved.
+ * SPDX-License-Identifier: MIT
+ * For full license text, see the LICENSE file in the repo root or https://opensource.org/licenses/MIT
+ */
+
+import StyledComponent from 'perf-benchmarks-components/dist/dom/benchmark/styledComponent.js';
+import { styledComponentBenchmark } from '../../../utils/styledComponentBenchmark';
+
+// Create 1k components with the same CSS in each component
+styledComponentBenchmark(`ss-benchmark-styled-component/create/1k/same`, StyledComponent);
diff --git a/packages/perf-benchmarks/src/__benchmarks__/engine-dom/benchmark-styled-component/styled-component-create-1k-different.benchmark.js b/packages/perf-benchmarks/src/__benchmarks__/engine-dom/benchmark-styled-component/styled-component-create-1k-different.benchmark.js
new file mode 100644
index 0000000000..d7052436f2
--- /dev/null
+++ b/packages/perf-benchmarks/src/__benchmarks__/engine-dom/benchmark-styled-component/styled-component-create-1k-different.benchmark.js
@@ -0,0 +1,12 @@
+/*
+ * Copyright (c) 2018, salesforce.com, inc.
+ * All rights reserved.
+ * SPDX-License-Identifier: MIT
+ * For full license text, see the LICENSE file in the repo root or https://opensource.org/licenses/MIT
+ */
+
+import components from 'perf-benchmarks-components/dist/dom/benchmark/styledComponents.js';
+import { styledComponentBenchmark } from '../../../utils/styledComponentBenchmark';
+
+// Create 1k components with different CSS in each component
+styledComponentBenchmark(`benchmark-styled-component/create/1k/different`, components);
diff --git a/packages/perf-benchmarks/src/__benchmarks__/engine-dom/benchmark-styled-component/styled-component-create-1k-same.benchmark.js b/packages/perf-benchmarks/src/__benchmarks__/engine-dom/benchmark-styled-component/styled-component-create-1k-same.benchmark.js
new file mode 100644
index 0000000000..7aed39fb3a
--- /dev/null
+++ b/packages/perf-benchmarks/src/__benchmarks__/engine-dom/benchmark-styled-component/styled-component-create-1k-same.benchmark.js
@@ -0,0 +1,12 @@
+/*
+ * Copyright (c) 2018, salesforce.com, inc.
+ * All rights reserved.
+ * SPDX-License-Identifier: MIT
+ * For full license text, see the LICENSE file in the repo root or https://opensource.org/licenses/MIT
+ */
+
+import StyledComponent from 'perf-benchmarks-components/dist/dom/benchmark/styledComponent.js';
+import { styledComponentBenchmark } from '../../../utils/styledComponentBenchmark';
+
+// Create 1k components with the same CSS in each component
+styledComponentBenchmark(`benchmark-styled-component/create/1k/same`, StyledComponent);
diff --git a/packages/perf-benchmarks/src/utils/styledComponentBenchmark.js b/packages/perf-benchmarks/src/utils/styledComponentBenchmark.js
new file mode 100644
index 0000000000..8885501ab3
--- /dev/null
+++ b/packages/perf-benchmarks/src/utils/styledComponentBenchmark.js
@@ -0,0 +1,35 @@
+/*
+ * Copyright (c) 2018, salesforce.com, inc.
+ * All rights reserved.
+ * SPDX-License-Identifier: MIT
+ * For full license text, see the LICENSE file in the repo root or https://opensource.org/licenses/MIT
+ */
+
+import { createElement } from 'lwc';
+import { destroyComponent } from './utils.js';
+import { benchmark, run, after } from './benchmark-framework.js';
+
+// Generic benchmark for styled components
+export function styledComponentBenchmark(name, componentOrComponents) {
+    benchmark(name, () => {
+        const elms = [];
+
+        const isArray = Array.isArray(componentOrComponents);
+
+        run(async () => {
+            for (let i = 0; i < 1000; i++) {
+                const elm = createElement(isArray ? `styled-component${i}` : 'styled-component', {
+                    is: isArray ? componentOrComponents[i] : componentOrComponents,
+                });
+                document.body.appendChild(elm);
+                elms.push(elm);
+            }
+        });
+
+        after(() => {
+            for (const elm of elms) {
+                destroyComponent(elm);
+            }
+        });
+    });
+}