diff --git a/docs/user-guide/rules/list.md b/docs/user-guide/rules/list.md
index be7dc668d7..418456e88e 100644
--- a/docs/user-guide/rules/list.md
+++ b/docs/user-guide/rules/list.md
@@ -198,6 +198,7 @@ Within each cateogory, the rules are grouped by the [_thing_](http://apps.workfl
 - [`selector-nested-pattern`](../../../lib/rules/selector-nested-pattern/README.md): Specify a pattern for the selectors of rules nested within rules.
 - [`selector-no-qualifying-type`](../../../lib/rules/selector-no-qualifying-type/README.md): Disallow qualifying a selector by type.
 - [`selector-no-vendor-prefix`](../../../lib/rules/selector-no-vendor-prefix/README.md): Disallow vendor prefixes for selectors (Autofixable).
+- [`selector-not-notation`](../../../lib/rules/selector-not-notation/README.md): Specify simple or complex notation for the usage of `:not()`.
 - [`selector-pseudo-class-allowed-list`](../../../lib/rules/selector-pseudo-class-allowed-list/README.md): Specify a list of allowed pseudo-class selectors.
 - [`selector-pseudo-class-disallowed-list`](../../../lib/rules/selector-pseudo-class-disallowed-list/README.md): Specify a list of disallowed pseudo-class selectors.
 - [`selector-pseudo-element-allowed-list`](../../../lib/rules/selector-pseudo-element-allowed-list/README.md): Specify a list of allowed pseudo-element selectors.
diff --git a/lib/rules/index.js b/lib/rules/index.js
index a300e747b4..238b24a36c 100644
--- a/lib/rules/index.js
+++ b/lib/rules/index.js
@@ -214,6 +214,7 @@ const rules = {
 	'selector-nested-pattern': importLazy('./selector-nested-pattern'),
 	'selector-no-qualifying-type': importLazy('./selector-no-qualifying-type'),
 	'selector-no-vendor-prefix': importLazy('./selector-no-vendor-prefix'),
+	'selector-not-notation': importLazy('./selector-not-notation'),
 	'selector-pseudo-class-allowed-list': importLazy('./selector-pseudo-class-allowed-list'),
 	'selector-pseudo-class-case': importLazy('./selector-pseudo-class-case'),
 	'selector-pseudo-class-disallowed-list': importLazy('./selector-pseudo-class-disallowed-list'),
diff --git a/lib/rules/selector-not-notation/README.md b/lib/rules/selector-not-notation/README.md
new file mode 100644
index 0000000000..d37c6d50de
--- /dev/null
+++ b/lib/rules/selector-not-notation/README.md
@@ -0,0 +1,57 @@
+# selector-not-notation
+
+## Options
+
+`string`: `"simple"|"complex"`
+
+### `"simple"`
+
+The following patterns are considered problems:
+
+<!-- prettier-ignore -->
+```css
+:not(a, div) {}
+```
+
+<!-- prettier-ignore -->
+```css
+:not(a.foo) {}
+```
+
+The following patterns are _not_ considered problems:
+
+<!-- prettier-ignore -->
+```css
+:not(a):not(div) {}
+```
+
+<!-- prettier-ignore -->
+```css
+:not(a) {}
+```
+
+### `"complex"`
+
+The following pattern is considered a problem:
+
+<!-- prettier-ignore -->
+```css
+:not(a):not(div) {}
+```
+
+The following patterns are _not_ considered problems:
+
+<!-- prettier-ignore -->
+```css
+:not(a, div) {}
+```
+
+<!-- prettier-ignore -->
+```css
+:not(a.foo) {}
+```
+
+<!-- prettier-ignore -->
+```css
+:not(a).foo:not(:empty) {}
+```
diff --git a/lib/rules/selector-not-notation/__tests__/index.js b/lib/rules/selector-not-notation/__tests__/index.js
new file mode 100644
index 0000000000..3f69361911
--- /dev/null
+++ b/lib/rules/selector-not-notation/__tests__/index.js
@@ -0,0 +1,95 @@
+'use strict';
+
+const { messages, ruleName } = require('..');
+
+testRule({
+	ruleName,
+	config: ['simple'],
+	fix: false,
+
+	accept: [
+		{
+			code: ':not() {}',
+		},
+		{
+			code: ':not( a ) {}',
+		},
+		{
+			code: ':nOt(a) {}',
+		},
+		{
+			code: ':not(*) {}',
+		},
+		{
+			code: ':not(:link) {}',
+		},
+		{
+			code: ':not(.foo) {}',
+		},
+		{
+			code: ':not([title]) {}',
+		},
+	],
+
+	reject: [
+		{
+			code: ':not(:not()) {}',
+			fixed: ':not()',
+			message: messages.expected('simple'),
+			line: 1,
+			column: 1,
+		},
+		{
+			code: ':not(::before) {}',
+			fixed: ':not()',
+			message: messages.expected('simple'),
+			line: 1,
+			column: 1,
+		},
+		{
+			code: ':not(a, div) {}',
+			fixed: ':not(a):not(div) {}',
+			message: messages.expected('simple'),
+			line: 1,
+			column: 1,
+		},
+		{
+			code: ':not(a.foo) {}',
+			unfixable: true,
+			message: messages.expected('simple'),
+			line: 1,
+			column: 1,
+		},
+	],
+});
+
+testRule({
+	ruleName,
+	config: ['complex'],
+	fix: false,
+
+	accept: [
+		{
+			code: ':not()::after {}',
+		},
+		{
+			code: ':not(a, div) {}',
+		},
+		{
+			code: ':not(a.foo) {}',
+		},
+		{
+			code: ':not(a).foo:not(:empty) {}',
+		},
+	],
+
+	reject: [
+		{
+			code: ':not(.foo):not(a) {}',
+			fixed: ':not(.foo, a) {} {}',
+			message: messages.expected('complex'),
+			line: 1,
+			column: 11,
+		},
+	],
+});
diff --git a/lib/rules/selector-not-notation/index.js b/lib/rules/selector-not-notation/index.js
new file mode 100644
index 0000000000..27feed0c2c
--- /dev/null
+++ b/lib/rules/selector-not-notation/index.js
@@ -0,0 +1,128 @@
+'use strict';
+
+const isStandardSyntaxRule = require('../../utils/isStandardSyntaxRule');
+const parseSelector = require('../../utils/parseSelector');
+const report = require('../../utils/report');
+const ruleMessages = require('../../utils/ruleMessages');
+const validateOptions = require('../../utils/validateOptions');
+const {
+	isPseudoClass: buggyIsPseudoClass, // cf https://github.com/postcss/postcss-selector-parser/blob/master/src/selectors/guards.js#L52
+	isAttribute,
+	isClassName,
+	isUniversal,
+	isIdentifier,
+	isTag,
+} = require('postcss-selector-parser');
+
+const ruleName = 'selector-not-notation';
+const messages = ruleMessages(ruleName, {
+	expected: (type) => `Expected ${type} :not() pseudo-class notation`,
+});
+const meta = { url: 'https://stylelint.io/user-guide/rules/list/selector-not-notation' };
+
+/** @typedef {import('postcss-selector-parser').Node} Node */
+/** @typedef {import('postcss-selector-parser').Selector} Selector */
+
+/**
+ * @param {Node} node
+ * @returns {boolean}
+ */
+const isPseudoClass = (node) =>
+	buggyIsPseudoClass(node) &&
+	node.value.toLowerCase() !== ':first-line' &&
+	node.value.toLowerCase() !== ':first-letter';
+
+/**
+ * @param {Node} node
+ * @returns {boolean}
+ */
+const isSimpleSelector = (node) =>
+	isPseudoClass(node) ||
+	isAttribute(node) ||
+	isClassName(node) ||
+	isUniversal(node) ||
+	isIdentifier(node) ||
+	isTag(node);
+
+/**
+ * @param {Node} node
+ * @returns {boolean}
+ */
+const isNot = (node) =>
+	isPseudoClass(node) && node.value !== undefined && node.value.toLowerCase() === ':not';
+
+/**
+ * @param {Selector[]} list
+ * @returns {boolean}
+ */
+const isSimple = (list) => {
+	if (list.length > 1) return false;
+
+	const [first, second] = list[0].nodes; // list is never empty
+
+	if (!first) return true;
+
+	if (second) return false;
+
+	return isSimpleSelector(first) && !isNot(first);
+};
+
+/** @type {import('stylelint').Rule} */
+const rule = (primary, _, context) => {
+	return (root, result) => {
+		const validOptions = validateOptions(result, ruleName, {
+			actual: primary,
+			possible: ['simple', 'complex'],
+		});
+
+		if (!validOptions) {
+			return;
+		}
+
+		root.walkRules((ruleNode) => {
+			if (!isStandardSyntaxRule(ruleNode)) {
+				return;
+			}
+
+			const selector = ruleNode.selector;
+
+			/*const fixedSelector = */ parseSelector(selector, result, ruleNode, (container) => {
+				container.walkPseudos((pseudo) => {
+					if (!isNot(pseudo)) return;
+
+					if (primary === 'complex') {
+						const prev = pseudo.prev();
+						const hasConsecutiveNot = prev && isNot(prev);
+
+						if (!hasConsecutiveNot) return;
+
+						if (context.fix) {
+							/* TODO */
+							return;
+						}
+					} else {
+						if (isSimple(pseudo.nodes)) return;
+
+						if (context.fix) {
+							/* TODO */
+							return;
+						}
+					}
+
+					report({
+						message: messages.expected(primary),
+						node: ruleNode,
+						index: pseudo.sourceIndex,
+						result,
+						ruleName,
+					});
+				});
+			});
+		});
+	};
+};
+
+rule.ruleName = ruleName;
+rule.messages = messages;
+rule.meta = meta;
+module.exports = rule;