diff --git a/.stylelintignore b/.stylelintignore
new file mode 100644
index 00000000000000..06bb87c852b4a0
--- /dev/null
+++ b/.stylelintignore
@@ -0,0 +1 @@
+packages/stylelint-config/test
diff --git a/.stylelintrc.json b/.stylelintrc.json
index 3d4ff66523fe3b..c7a2d1db18a460 100644
--- a/.stylelintrc.json
+++ b/.stylelintrc.json
@@ -1,5 +1,5 @@
 {
-	"extends": "@wordpress/stylelint-config",
+	"extends": "@wordpress/stylelint-config/scss",
 	"rules": {
 		"at-rule-empty-line-before": null,
 		"at-rule-no-unknown": null,
@@ -9,6 +9,17 @@
 		"no-descending-specificity": null,
 		"rule-empty-line-before": null,
 		"selector-class-pattern": null,
-		"value-keyword-case": null
+		"value-keyword-case": null,
+		"scss/operator-no-unspaced": null,
+		"scss/selector-no-redundant-nesting-selector": null,
+		"scss/at-import-partial-extension": null,
+		"scss/no-global-function-names": null,
+		"scss/comment-no-empty": null,
+		"scss/at-extend-no-missing-placeholder": null,
+		"scss/operator-no-newline-after": null,
+		"scss/at-if-closing-brace-newline-after": null,
+		"scss/at-else-empty-line-before": null,
+		"scss/at-if-closing-brace-space-after": null,
+		"no-invalid-position-at-import-rule": null
 	}
 }
diff --git a/docs/contributors/folder-structure.md b/docs/contributors/folder-structure.md
index 5e5648d8e2f7d5..9cee302794cdab 100644
--- a/docs/contributors/folder-structure.md
+++ b/docs/contributors/folder-structure.md
@@ -15,6 +15,7 @@ The following snippet explains how the Gutenberg repository is structured omitti
     ├── .jshintignore
     ├── .eslintignore
     ├── .prettierrc.js
+    ├── .stylelintignore
     ├── .stylelintrc.json
     ├── .markdownlintignore
     ├── .npmpackagejsonlintrc.json
diff --git a/package-lock.json b/package-lock.json
index f52d14b34c2b5c..86e9c05a166644 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -13902,113 +13902,6 @@
 				}
 			}
 		},
-		"@stylelint/postcss-css-in-js": {
-			"version": "0.37.2",
-			"resolved": "https://registry.npmjs.org/@stylelint/postcss-css-in-js/-/postcss-css-in-js-0.37.2.tgz",
-			"integrity": "sha512-nEhsFoJurt8oUmieT8qy4nk81WRHmJynmVwn/Vts08PL9fhgIsMhk1GId5yAN643OzqEEb5S/6At2TZW7pqPDA==",
-			"dev": true,
-			"requires": {
-				"@babel/core": ">=7.9.0"
-			}
-		},
-		"@stylelint/postcss-markdown": {
-			"version": "0.36.2",
-			"resolved": "https://registry.npmjs.org/@stylelint/postcss-markdown/-/postcss-markdown-0.36.2.tgz",
-			"integrity": "sha512-2kGbqUVJUGE8dM+bMzXG/PYUWKkjLIkRLWNh39OaADkiabDRdw8ATFCgbMz5xdIcvwspPAluSL7uY+ZiTWdWmQ==",
-			"dev": true,
-			"requires": {
-				"remark": "^13.0.0",
-				"unist-util-find-all-after": "^3.0.2"
-			},
-			"dependencies": {
-				"is-buffer": {
-					"version": "2.0.5",
-					"resolved": "https://registry.npmjs.org/is-buffer/-/is-buffer-2.0.5.tgz",
-					"integrity": "sha512-i2R6zNFDwgEHJyQUtJEk0XFi1i0dPFn/oqjK3/vPCcDeJvW5NQ83V8QbicfF1SupOaB0h8ntgBC2YiE7dfyctQ==",
-					"dev": true
-				},
-				"is-plain-obj": {
-					"version": "2.1.0",
-					"resolved": "https://registry.npmjs.org/is-plain-obj/-/is-plain-obj-2.1.0.tgz",
-					"integrity": "sha512-YWnfyRwxL/+SsrWYfOpUtz5b3YD+nyfkHvjbcanzk8zgyO4ASD67uVMRt8k5bM4lLMDnXfriRhOpemw+NfT1eA==",
-					"dev": true
-				},
-				"remark": {
-					"version": "13.0.0",
-					"resolved": "https://registry.npmjs.org/remark/-/remark-13.0.0.tgz",
-					"integrity": "sha512-HDz1+IKGtOyWN+QgBiAT0kn+2s6ovOxHyPAFGKVE81VSzJ+mq7RwHFledEvB5F1p4iJvOah/LOKdFuzvRnNLCA==",
-					"dev": true,
-					"requires": {
-						"remark-parse": "^9.0.0",
-						"remark-stringify": "^9.0.0",
-						"unified": "^9.1.0"
-					}
-				},
-				"remark-parse": {
-					"version": "9.0.0",
-					"resolved": "https://registry.npmjs.org/remark-parse/-/remark-parse-9.0.0.tgz",
-					"integrity": "sha512-geKatMwSzEXKHuzBNU1z676sGcDcFoChMK38TgdHJNAYfFtsfHDQG7MoJAjs6sgYMqyLduCYWDIWZIxiPeafEw==",
-					"dev": true,
-					"requires": {
-						"mdast-util-from-markdown": "^0.8.0"
-					}
-				},
-				"remark-stringify": {
-					"version": "9.0.1",
-					"resolved": "https://registry.npmjs.org/remark-stringify/-/remark-stringify-9.0.1.tgz",
-					"integrity": "sha512-mWmNg3ZtESvZS8fv5PTvaPckdL4iNlCHTt8/e/8oN08nArHRHjNZMKzA/YW3+p7/lYqIw4nx1XsjCBo/AxNChg==",
-					"dev": true,
-					"requires": {
-						"mdast-util-to-markdown": "^0.6.0"
-					}
-				},
-				"unified": {
-					"version": "9.2.1",
-					"resolved": "https://registry.npmjs.org/unified/-/unified-9.2.1.tgz",
-					"integrity": "sha512-juWjuI8Z4xFg8pJbnEZ41b5xjGUWGHqXALmBZ3FC3WX0PIx1CZBIIJ6mXbYMcf6Yw4Fi0rFUTA1cdz/BglbOhA==",
-					"dev": true,
-					"requires": {
-						"bail": "^1.0.0",
-						"extend": "^3.0.0",
-						"is-buffer": "^2.0.0",
-						"is-plain-obj": "^2.0.0",
-						"trough": "^1.0.0",
-						"vfile": "^4.0.0"
-					}
-				},
-				"unist-util-stringify-position": {
-					"version": "2.0.3",
-					"resolved": "https://registry.npmjs.org/unist-util-stringify-position/-/unist-util-stringify-position-2.0.3.tgz",
-					"integrity": "sha512-3faScn5I+hy9VleOq/qNbAd6pAx7iH5jYBMS9I1HgQVijz/4mv5Bvw5iw1sC/90CODiKo81G/ps8AJrISn687g==",
-					"dev": true,
-					"requires": {
-						"@types/unist": "^2.0.2"
-					}
-				},
-				"vfile": {
-					"version": "4.2.1",
-					"resolved": "https://registry.npmjs.org/vfile/-/vfile-4.2.1.tgz",
-					"integrity": "sha512-O6AE4OskCG5S1emQ/4gl8zK586RqA3srz3nfK/Viy0UPToBc5Trp9BVFb1u0CjsKrAWwnpr4ifM/KBXPWwJbCA==",
-					"dev": true,
-					"requires": {
-						"@types/unist": "^2.0.0",
-						"is-buffer": "^2.0.0",
-						"unist-util-stringify-position": "^2.0.0",
-						"vfile-message": "^2.0.0"
-					}
-				},
-				"vfile-message": {
-					"version": "2.0.4",
-					"resolved": "https://registry.npmjs.org/vfile-message/-/vfile-message-2.0.4.tgz",
-					"integrity": "sha512-DjssxRGkMvifUOJre00juHoP9DPWuzjxKuMDrhNbk2TdaYYBNMStsNhEOt3idrtI12VQYM/1+iM0KOzXi4pxwQ==",
-					"dev": true,
-					"requires": {
-						"@types/unist": "^2.0.0",
-						"unist-util-stringify-position": "^2.0.0"
-					}
-				}
-			}
-		},
 		"@svgr/babel-plugin-add-jsx-attribute": {
 			"version": "5.4.0",
 			"resolved": "https://registry.npmjs.org/@svgr/babel-plugin-add-jsx-attribute/-/babel-plugin-add-jsx-attribute-5.4.0.tgz",
@@ -17034,8 +16927,8 @@
 				"minimist": "^1.2.0",
 				"npm-package-json-lint": "^5.0.0",
 				"npm-packlist": "^3.0.0",
-				"postcss": "^8.2.15",
-				"postcss-loader": "^6.1.1",
+				"postcss": "^8.4.5",
+				"postcss-loader": "^6.2.1",
 				"prettier": "npm:wp-prettier@2.2.1-beta-1",
 				"puppeteer-core": "^11.0.0",
 				"react-refresh": "^0.10.0",
@@ -17044,13 +16937,25 @@
 				"sass": "^1.35.2",
 				"sass-loader": "^12.1.0",
 				"source-map-loader": "^3.0.0",
-				"stylelint": "^13.8.0",
+				"stylelint": "^14.2.0",
 				"terser-webpack-plugin": "^5.1.4",
 				"url-loader": "^4.1.1",
 				"webpack": "^5.47.1",
 				"webpack-bundle-analyzer": "^4.4.2",
 				"webpack-cli": "^4.9.1",
 				"webpack-dev-server": "^4.4.0"
+			},
+			"dependencies": {
+				"nanoid": {
+					"version": "3.2.0",
+					"resolved": "https://registry.npmjs.org/nanoid/-/nanoid-3.2.0.tgz",
+					"integrity": "sha512-fmsZYa9lpn69Ad5eDn7FMcnnSR+8R34W9qJEijxYhTbfOWzr22n1QxCMzXLK+ODyW2973V3Fux959iQoUxzUIA=="
+				},
+				"source-map-js": {
+					"version": "1.0.2",
+					"resolved": "https://registry.npmjs.org/source-map-js/-/source-map-js-1.0.2.tgz",
+					"integrity": "sha512-R0XvVJ9WusLiqTCEiGCmICCMplcCkIwwR11mOSD9CR5u+IXYdiseeEuXCVAjS54zqwkLcPNnmU4OeJ6tUrWhDw=="
+				}
 			}
 		},
 		"@wordpress/server-side-render": {
@@ -17081,9 +16986,8 @@
 			"version": "file:packages/stylelint-config",
 			"dev": true,
 			"requires": {
-				"stylelint-config-recommended": "^3.0.0",
-				"stylelint-config-recommended-scss": "^4.2.0",
-				"stylelint-scss": "^3.17.2"
+				"stylelint-config-recommended": "^6.0.0",
+				"stylelint-config-recommended-scss": "^5.0.2"
 			}
 		},
 		"@wordpress/token-list": {
@@ -35707,15 +35611,6 @@
 			"integrity": "sha1-L0SUrIkZ43Z8XLtpHp9GMyQoXUM=",
 			"dev": true
 		},
-		"gonzales-pe": {
-			"version": "4.3.0",
-			"resolved": "https://registry.npmjs.org/gonzales-pe/-/gonzales-pe-4.3.0.tgz",
-			"integrity": "sha512-otgSPpUmdWJ43VXyiNgEYE4luzHCL2pz4wQ0OnDluC6Eg4Ko3Vexy/SrSynglw/eR+OhkzmqFCZa/OFa/RgAOQ==",
-			"dev": true,
-			"requires": {
-				"minimist": "^1.2.5"
-			}
-		},
 		"good-listener": {
 			"version": "1.2.2",
 			"resolved": "https://registry.npmjs.org/good-listener/-/good-listener-1.2.2.tgz",
@@ -41627,9 +41522,9 @@
 			"dev": true
 		},
 		"known-css-properties": {
-			"version": "0.20.0",
-			"resolved": "https://registry.npmjs.org/known-css-properties/-/known-css-properties-0.20.0.tgz",
-			"integrity": "sha512-URvsjaA9ypfreqJ2/ylDr5MUERhJZ+DhguoWRr2xgS5C7aGCalXo+ewL+GixgKBfhT2vuL02nbIgNGqVWgTOYw==",
+			"version": "0.24.0",
+			"resolved": "https://registry.npmjs.org/known-css-properties/-/known-css-properties-0.24.0.tgz",
+			"integrity": "sha512-RTSoaUAfLvpR357vWzAz/50Q/BmHfmE6ETSWfutT0AJiw10e6CmcdYRQJlLRd95B53D0Y2aD1jSxD3V3ySF+PA==",
 			"dev": true
 		},
 		"language-subtag-registry": {
@@ -42343,6 +42238,12 @@
 			"resolved": "https://registry.npmjs.org/lodash.throttle/-/lodash.throttle-4.1.1.tgz",
 			"integrity": "sha1-wj6RtxAkKscMN/HhzaknTMOb8vQ="
 		},
+		"lodash.truncate": {
+			"version": "4.4.2",
+			"resolved": "https://registry.npmjs.org/lodash.truncate/-/lodash.truncate-4.4.2.tgz",
+			"integrity": "sha1-WjUNoLERO4N+z//VgSy+WNbq4ZM=",
+			"dev": true
+		},
 		"lodash.union": {
 			"version": "4.6.0",
 			"resolved": "https://registry.npmjs.org/lodash.union/-/lodash.union-4.6.0.tgz",
@@ -43011,50 +42912,6 @@
 				}
 			}
 		},
-		"mdast-util-from-markdown": {
-			"version": "0.8.4",
-			"resolved": "https://registry.npmjs.org/mdast-util-from-markdown/-/mdast-util-from-markdown-0.8.4.tgz",
-			"integrity": "sha512-jj891B5pV2r63n2kBTFh8cRI2uR9LQHsXG1zSDqfhXkIlDzrTcIlbB5+5aaYEkl8vOPIOPLf8VT7Ere1wWTMdw==",
-			"dev": true,
-			"requires": {
-				"@types/mdast": "^3.0.0",
-				"mdast-util-to-string": "^2.0.0",
-				"micromark": "~2.11.0",
-				"parse-entities": "^2.0.0",
-				"unist-util-stringify-position": "^2.0.0"
-			},
-			"dependencies": {
-				"mdast-util-to-string": {
-					"version": "2.0.0",
-					"resolved": "https://registry.npmjs.org/mdast-util-to-string/-/mdast-util-to-string-2.0.0.tgz",
-					"integrity": "sha512-AW4DRS3QbBayY/jJmD8437V1Gombjf8RSOUCMFBuo5iHi58AGEgVCKQ+ezHkZZDpAQS75hcBMpLqjpJTjtUL7w==",
-					"dev": true
-				},
-				"parse-entities": {
-					"version": "2.0.0",
-					"resolved": "https://registry.npmjs.org/parse-entities/-/parse-entities-2.0.0.tgz",
-					"integrity": "sha512-kkywGpCcRYhqQIchaWqZ875wzpS/bMKhz5HnN3p7wveJTkTtyAB/AlnS0f8DFSqYW1T82t6yEAkEcB+A1I3MbQ==",
-					"dev": true,
-					"requires": {
-						"character-entities": "^1.0.0",
-						"character-entities-legacy": "^1.0.0",
-						"character-reference-invalid": "^1.0.0",
-						"is-alphanumerical": "^1.0.0",
-						"is-decimal": "^1.0.0",
-						"is-hexadecimal": "^1.0.0"
-					}
-				},
-				"unist-util-stringify-position": {
-					"version": "2.0.3",
-					"resolved": "https://registry.npmjs.org/unist-util-stringify-position/-/unist-util-stringify-position-2.0.3.tgz",
-					"integrity": "sha512-3faScn5I+hy9VleOq/qNbAd6pAx7iH5jYBMS9I1HgQVijz/4mv5Bvw5iw1sC/90CODiKo81G/ps8AJrISn687g==",
-					"dev": true,
-					"requires": {
-						"@types/unist": "^2.0.2"
-					}
-				}
-			}
-		},
 		"mdast-util-inject": {
 			"version": "1.1.0",
 			"resolved": "https://registry.npmjs.org/mdast-util-inject/-/mdast-util-inject-1.1.0.tgz",
@@ -43109,42 +42966,6 @@
 				}
 			}
 		},
-		"mdast-util-to-markdown": {
-			"version": "0.6.1",
-			"resolved": "https://registry.npmjs.org/mdast-util-to-markdown/-/mdast-util-to-markdown-0.6.1.tgz",
-			"integrity": "sha512-4qJtZ0qdyYeexAXoOZiU0uHIFVncJAmCkHkSluAsvDaVWODtPyNEo9I1ns0T4ulxu2EHRH5u/bt1cV0pdHCX+A==",
-			"dev": true,
-			"requires": {
-				"@types/unist": "^2.0.0",
-				"longest-streak": "^2.0.0",
-				"mdast-util-to-string": "^2.0.0",
-				"parse-entities": "^2.0.0",
-				"repeat-string": "^1.0.0",
-				"zwitch": "^1.0.0"
-			},
-			"dependencies": {
-				"mdast-util-to-string": {
-					"version": "2.0.0",
-					"resolved": "https://registry.npmjs.org/mdast-util-to-string/-/mdast-util-to-string-2.0.0.tgz",
-					"integrity": "sha512-AW4DRS3QbBayY/jJmD8437V1Gombjf8RSOUCMFBuo5iHi58AGEgVCKQ+ezHkZZDpAQS75hcBMpLqjpJTjtUL7w==",
-					"dev": true
-				},
-				"parse-entities": {
-					"version": "2.0.0",
-					"resolved": "https://registry.npmjs.org/parse-entities/-/parse-entities-2.0.0.tgz",
-					"integrity": "sha512-kkywGpCcRYhqQIchaWqZ875wzpS/bMKhz5HnN3p7wveJTkTtyAB/AlnS0f8DFSqYW1T82t6yEAkEcB+A1I3MbQ==",
-					"dev": true,
-					"requires": {
-						"character-entities": "^1.0.0",
-						"character-entities-legacy": "^1.0.0",
-						"character-reference-invalid": "^1.0.0",
-						"is-alphanumerical": "^1.0.0",
-						"is-decimal": "^1.0.0",
-						"is-hexadecimal": "^1.0.0"
-					}
-				}
-			}
-		},
 		"mdast-util-to-string": {
 			"version": "1.0.5",
 			"resolved": "https://registry.npmjs.org/mdast-util-to-string/-/mdast-util-to-string-1.0.5.tgz",
@@ -47515,32 +47336,26 @@
 			"integrity": "sha1-AerA/jta9xoqbAL+q7jB/vfgDqs="
 		},
 		"postcss": {
-			"version": "8.2.15",
-			"resolved": "https://registry.npmjs.org/postcss/-/postcss-8.2.15.tgz",
-			"integrity": "sha512-2zO3b26eJD/8rb106Qu2o7Qgg52ND5HPjcyQiK2B98O388h43A448LCslC0dI2P97wCAQRJsFvwTRcXxTKds+Q==",
+			"version": "8.4.5",
+			"resolved": "https://registry.npmjs.org/postcss/-/postcss-8.4.5.tgz",
+			"integrity": "sha512-jBDboWM8qpaqwkMwItqTQTiFikhs/67OYVvblFFTM7MrZjt6yMKd6r2kgXizEbTTljacm4NldIlZnhbjr84QYg==",
 			"dev": true,
 			"requires": {
-				"colorette": "^1.2.2",
-				"nanoid": "^3.1.23",
-				"source-map": "^0.6.1"
+				"nanoid": "^3.1.30",
+				"picocolors": "^1.0.0",
+				"source-map-js": "^1.0.1"
 			},
 			"dependencies": {
-				"colorette": {
-					"version": "1.2.2",
-					"resolved": "https://registry.npmjs.org/colorette/-/colorette-1.2.2.tgz",
-					"integrity": "sha512-MKGMzyfeuutC/ZJ1cba9NqcNpfeqMUcYmyF1ZFY6/Cn7CNSAKx6a+s48sqLqyAiZuaP2TcqMhoo+dlwFnVxT9w==",
-					"dev": true
-				},
 				"nanoid": {
-					"version": "3.1.23",
-					"resolved": "https://registry.npmjs.org/nanoid/-/nanoid-3.1.23.tgz",
-					"integrity": "sha512-FiB0kzdP0FFVGDKlRLEQ1BgDzU87dy5NnzjeW9YZNt+/c3+q82EQDUwniSAUxp/F0gFNI1ZhKU1FqYsMuqZVnw==",
+					"version": "3.2.0",
+					"resolved": "https://registry.npmjs.org/nanoid/-/nanoid-3.2.0.tgz",
+					"integrity": "sha512-fmsZYa9lpn69Ad5eDn7FMcnnSR+8R34W9qJEijxYhTbfOWzr22n1QxCMzXLK+ODyW2973V3Fux959iQoUxzUIA==",
 					"dev": true
 				},
-				"source-map": {
-					"version": "0.6.1",
-					"resolved": "https://registry.npmjs.org/source-map/-/source-map-0.6.1.tgz",
-					"integrity": "sha512-UjgapumWlbMhkBgzT7Ykc5YXUT46F0iKu8SGXq0bcwP5dz/h0Plj6enJqjz1Zbq2l5WaqYnrVbwWOWMyF3F47g==",
+				"source-map-js": {
+					"version": "1.0.2",
+					"resolved": "https://registry.npmjs.org/source-map-js/-/source-map-js-1.0.2.tgz",
+					"integrity": "sha512-R0XvVJ9WusLiqTCEiGCmICCMplcCkIwwR11mOSD9CR5u+IXYdiseeEuXCVAjS54zqwkLcPNnmU4OeJ6tUrWhDw==",
 					"dev": true
 				}
 			}
@@ -47657,118 +47472,25 @@
 				}
 			}
 		},
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-			"resolved": "https://registry.npmjs.org/stylelint-scss/-/stylelint-scss-3.17.2.tgz",
-			"integrity": "sha512-e0dmxqsofy/HZj4urcGSJw4S6yHDJxiQdT20/1ciCsd5lomisa7YM4+Qtt1EG4hsqEG1dbEeF855tec1UyqcSA==",
+			"version": "4.1.0",
+			"resolved": "https://registry.npmjs.org/stylelint-scss/-/stylelint-scss-4.1.0.tgz",
+			"integrity": "sha512-BNYTo7MMamhFOlcaAWp2dMpjg6hPyM/FFqfDIYzmYVLMmQJqc8lWRIiTqP4UX5bresj9Vo0dKC6odSh43VP2NA==",
 			"dev": true,
 			"requires": {
-				"lodash": "^4.17.15",
+				"lodash": "^4.17.21",
 				"postcss-media-query-parser": "^0.2.3",
 				"postcss-resolve-nested-selector": "^0.1.1",
-				"postcss-selector-parser": "^6.0.2",
+				"postcss-selector-parser": "^6.0.6",
 				"postcss-value-parser": "^4.1.0"
 			},
 			"dependencies": {
+				"postcss-selector-parser": {
+					"version": "6.0.8",
+					"resolved": "https://registry.npmjs.org/postcss-selector-parser/-/postcss-selector-parser-6.0.8.tgz",
+					"integrity": "sha512-D5PG53d209Z1Uhcc0qAZ5U3t5HagH3cxu+WLZ22jt3gLUpXM4eXXfiO14jiDWST3NNooX/E8wISfOhZ9eIjGTQ==",
+					"dev": true,
+					"requires": {
+						"cssesc": "^3.0.0",
+						"util-deprecate": "^1.0.2"
+					}
+				},
 				"postcss-value-parser": {
-					"version": "4.1.0",
-					"resolved": "https://registry.npmjs.org/postcss-value-parser/-/postcss-value-parser-4.1.0.tgz",
-					"integrity": "sha512-97DXOFbQJhk71ne5/Mt6cOu6yxsSfM0QGQyl0L25Gca4yGWEGJaig7l7gbCX623VqTBNGLRLaVUCnNkcedlRSQ==",
+					"version": "4.2.0",
+					"resolved": "https://registry.npmjs.org/postcss-value-parser/-/postcss-value-parser-4.2.0.tgz",
+					"integrity": "sha512-1NNCs6uurfkVbeXG4S8JFT9t19m45ICnif8zWLd5oPSZ50QnwMfK+H3jv408d4jw/7Bttv5axS5IiHoLaVNHeQ==",
 					"dev": true
 				}
 			}
@@ -55319,65 +54896,6 @@
 			"resolved": "https://registry.npmjs.org/sudo-prompt/-/sudo-prompt-9.2.1.tgz",
 			"integrity": "sha512-Mu7R0g4ig9TUuGSxJavny5Rv0egCEtpZRNMrZaYS1vxkiIxGiGUwoezU3LazIQ+KE04hTrTfNPgxU5gzi7F5Pw=="
 		},
-		"sugarss": {
-			"version": "2.0.0",
-			"resolved": "https://registry.npmjs.org/sugarss/-/sugarss-2.0.0.tgz",
-			"integrity": "sha512-WfxjozUk0UVA4jm+U1d736AUpzSrNsQcIbyOkoE364GrtWmIrFdk5lksEupgWMD4VaT/0kVx1dobpiDumSgmJQ==",
-			"dev": true,
-			"requires": {
-				"postcss": "^7.0.2"
-			},
-			"dependencies": {
-				"chalk": {
-					"version": "2.4.2",
-					"resolved": "https://registry.npmjs.org/chalk/-/chalk-2.4.2.tgz",
-					"integrity": "sha512-Mti+f9lpJNcwF4tWV8/OrTTtF1gZi+f8FqlyAdouralcFWFQWF2+NgCHShjkCb+IFBLq9buZwE1xckQU4peSuQ==",
-					"dev": true,
-					"requires": {
-						"ansi-styles": "^3.2.1",
-						"escape-string-regexp": "^1.0.5",
-						"supports-color": "^5.3.0"
-					},
-					"dependencies": {
-						"supports-color": {
-							"version": "5.5.0",
-							"resolved": "https://registry.npmjs.org/supports-color/-/supports-color-5.5.0.tgz",
-							"integrity": "sha512-QjVjwdXIt408MIiAqCX4oUKsgU2EqAGzs2Ppkm4aQYbjm+ZEWEcW4SfFNTr4uMNZma0ey4f5lgLrkB0aX0QMow==",
-							"dev": true,
-							"requires": {
-								"has-flag": "^3.0.0"
-							}
-						}
-					}
-				},
-				"postcss": {
-					"version": "7.0.35",
-					"resolved": "https://registry.npmjs.org/postcss/-/postcss-7.0.35.tgz",
-					"integrity": "sha512-3QT8bBJeX/S5zKTTjTCIjRF3If4avAT6kqxcASlTWEtAFCb9NH0OUxNDfgZSWdP5fJnBYCMEWkIFfWeugjzYMg==",
-					"dev": true,
-					"requires": {
-						"chalk": "^2.4.2",
-						"source-map": "^0.6.1",
-						"supports-color": "^6.1.0"
-					}
-				},
-				"source-map": {
-					"version": "0.6.1",
-					"resolved": "https://registry.npmjs.org/source-map/-/source-map-0.6.1.tgz",
-					"integrity": "sha512-UjgapumWlbMhkBgzT7Ykc5YXUT46F0iKu8SGXq0bcwP5dz/h0Plj6enJqjz1Zbq2l5WaqYnrVbwWOWMyF3F47g==",
-					"dev": true
-				},
-				"supports-color": {
-					"version": "6.1.0",
-					"resolved": "https://registry.npmjs.org/supports-color/-/supports-color-6.1.0.tgz",
-					"integrity": "sha512-qe1jfm1Mg7Nq/NSh6XE24gPXROEVsWHxC1LIx//XNlD9iw7YZQGjZNjYN7xGaEG6iKdA8EtNFW6R0gjnVXp+wQ==",
-					"dev": true,
-					"requires": {
-						"has-flag": "^3.0.0"
-					}
-				}
-			}
-		},
 		"supports-color": {
 			"version": "5.4.0",
 			"resolved": "https://registry.npmjs.org/supports-color/-/supports-color-5.4.0.tgz",
@@ -55732,33 +55250,22 @@
 			"dev": true
 		},
 		"table": {
-			"version": "6.0.6",
-			"resolved": "https://registry.npmjs.org/table/-/table-6.0.6.tgz",
-			"integrity": "sha512-OInCtPmDNieVBkVFi6C8RwU2S2H0h8mF3e3TQK4nreaUNCpooQUkI+A/KuEkm5FawfhWIfNqG+qfelVVR+V00g==",
+			"version": "6.8.0",
+			"resolved": "https://registry.npmjs.org/table/-/table-6.8.0.tgz",
+			"integrity": "sha512-s/fitrbVeEyHKFa7mFdkuQMWlH1Wgw/yEXMt5xACT4ZpzWFluehAxRtUUQKPuWhaLAWhFcVx6w3oC8VKaUfPGA==",
 			"dev": true,
 			"requires": {
-				"ajv": "^7.0.2",
-				"lodash": "^4.17.20",
+				"ajv": "^8.0.1",
+				"lodash.truncate": "^4.4.2",
 				"slice-ansi": "^4.0.0",
-				"string-width": "^4.2.0"
+				"string-width": "^4.2.3",
+				"strip-ansi": "^6.0.1"
 			},
 			"dependencies": {
-				"ajv": {
-					"version": "7.0.3",
-					"resolved": "https://registry.npmjs.org/ajv/-/ajv-7.0.3.tgz",
-					"integrity": "sha512-R50QRlXSxqXcQP5SvKUrw8VZeypvo12i2IX0EeR5PiZ7bEKeHWgzgo264LDadUsCU42lTJVhFikTqJwNeH34gQ==",
-					"dev": true,
-					"requires": {
-						"fast-deep-equal": "^3.1.1",
-						"json-schema-traverse": "^1.0.0",
-						"require-from-string": "^2.0.2",
-						"uri-js": "^4.2.2"
-					}
-				},
 				"ansi-regex": {
-					"version": "5.0.0",
-					"resolved": "https://registry.npmjs.org/ansi-regex/-/ansi-regex-5.0.0.tgz",
-					"integrity": "sha512-bY6fj56OUQ0hU1KjFNDQuJFezqKdrAyFdIevADiqrWHwSlbmBNMHp5ak2f40Pm8JTFyM2mqxkG6ngkHO11f/lg==",
+					"version": "5.0.1",
+					"resolved": "https://registry.npmjs.org/ansi-regex/-/ansi-regex-5.0.1.tgz",
+					"integrity": "sha512-quJQXlTSUGL2LH9SUXo8VwsY4soanhgo6LNSm84E1LBcE8s3O0wpdiRzyR9z/ZZJMlMWv37qOOb9pdJlMUEKFQ==",
 					"dev": true
 				},
 				"ansi-styles": {
@@ -55797,30 +55304,12 @@
 					"integrity": "sha512-MSjYzcWNOA0ewAHpz0MxpYFvwg6yjy1NG3xteoqz644VCo/RPgnr1/GGt+ic3iJTzQ8Eu3TdM14SawnVUmGE6A==",
 					"dev": true
 				},
-				"fast-deep-equal": {
-					"version": "3.1.3",
-					"resolved": "https://registry.npmjs.org/fast-deep-equal/-/fast-deep-equal-3.1.3.tgz",
-					"integrity": "sha512-f3qQ9oQy9j2AhBe/H9VC91wLmKBCCU/gDOnKNAYG5hswO7BLKj09Hc5HYNz9cGI++xlpDCIgDaitVs03ATR84Q==",
-					"dev": true
-				},
 				"is-fullwidth-code-point": {
 					"version": "3.0.0",
 					"resolved": "https://registry.npmjs.org/is-fullwidth-code-point/-/is-fullwidth-code-point-3.0.0.tgz",
 					"integrity": "sha512-zymm5+u+sCsSWyD9qNaejV3DFvhCKclKdizYaJUuHA83RLjb7nSuGnddCHGv0hk+KY7BMAlsWeK4Ueg6EV6XQg==",
 					"dev": true
 				},
-				"json-schema-traverse": {
-					"version": "1.0.0",
-					"resolved": "https://registry.npmjs.org/json-schema-traverse/-/json-schema-traverse-1.0.0.tgz",
-					"integrity": "sha512-NM8/P9n3XjXhIZn1lLhkFaACTOURQXjWhV4BA/RnOv8xvgqtqpAX9IO4mRQxSx1Rlo4tqzeqb0sOlruaOy3dug==",
-					"dev": true
-				},
-				"lodash": {
-					"version": "4.17.20",
-					"resolved": "https://registry.npmjs.org/lodash/-/lodash-4.17.20.tgz",
-					"integrity": "sha512-PlhdFcillOINfeV7Ni6oF1TAEayyZBoZ8bcshTHqOYJYlrqzRK5hagpagky5o4HfCzzd1TRkXPMFq6cKk9rGmA==",
-					"dev": true
-				},
 				"slice-ansi": {
 					"version": "4.0.0",
 					"resolved": "https://registry.npmjs.org/slice-ansi/-/slice-ansi-4.0.0.tgz",
@@ -55833,23 +55322,23 @@
 					}
 				},
 				"string-width": {
-					"version": "4.2.0",
-					"resolved": "https://registry.npmjs.org/string-width/-/string-width-4.2.0.tgz",
-					"integrity": "sha512-zUz5JD+tgqtuDjMhwIg5uFVV3dtqZ9yQJlZVfq4I01/K5Paj5UHj7VyrQOJvzawSVlKpObApbfD0Ed6yJc+1eg==",
+					"version": "4.2.3",
+					"resolved": "https://registry.npmjs.org/string-width/-/string-width-4.2.3.tgz",
+					"integrity": "sha512-wKyQRQpjJ0sIp62ErSZdGsjMJWsap5oRNihHhu6G7JVO/9jIB6UyevL+tXuOqrng8j/cxKTWyWUwvSTriiZz/g==",
 					"dev": true,
 					"requires": {
 						"emoji-regex": "^8.0.0",
 						"is-fullwidth-code-point": "^3.0.0",
-						"strip-ansi": "^6.0.0"
+						"strip-ansi": "^6.0.1"
 					}
 				},
 				"strip-ansi": {
-					"version": "6.0.0",
-					"resolved": "https://registry.npmjs.org/strip-ansi/-/strip-ansi-6.0.0.tgz",
-					"integrity": "sha512-AuvKTrTfQNYNIctbR1K/YGTR1756GycPsg7b9bdV9Duqur4gv6aKqHXah67Z8ImS7WEz5QVcOtlfW2rZEugt6w==",
+					"version": "6.0.1",
+					"resolved": "https://registry.npmjs.org/strip-ansi/-/strip-ansi-6.0.1.tgz",
+					"integrity": "sha512-Y38VPSHcqkFrCpFnQ9vuSXmquuv5oXOKpGeT6aGrr3o3Gc9AlVa6JBfUSOCnbxGGZF+/0ooI7KrPuUSztUdU5A==",
 					"dev": true,
 					"requires": {
-						"ansi-regex": "^5.0.0"
+						"ansi-regex": "^5.0.1"
 					}
 				}
 			}
@@ -56938,23 +56427,6 @@
 			"integrity": "sha512-f98yt5pnlMWlzP539tPc4grGMsFaQQlP/vM396b00jngsiINumNmsY8rkXjfoi1c6QaM8nQ3vaGDuoKWbe/1Uw==",
 			"dev": true
 		},
-		"unist-util-find-all-after": {
-			"version": "3.0.2",
-			"resolved": "https://registry.npmjs.org/unist-util-find-all-after/-/unist-util-find-all-after-3.0.2.tgz",
-			"integrity": "sha512-xaTC/AGZ0rIM2gM28YVRAFPIZpzbpDtU3dRmp7EXlNVA8ziQc4hY3H7BHXM1J49nEmiqc3svnqMReW+PGqbZKQ==",
-			"dev": true,
-			"requires": {
-				"unist-util-is": "^4.0.0"
-			},
-			"dependencies": {
-				"unist-util-is": {
-					"version": "4.1.0",
-					"resolved": "https://registry.npmjs.org/unist-util-is/-/unist-util-is-4.1.0.tgz",
-					"integrity": "sha512-ZOQSsnce92GrxSqlnEEseX0gi7GH9zTJZ0p9dtu87WRb/37mMPO2Ilx1s/t9vBHrFhbgweUwb+t7cIn5dxPhZg==",
-					"dev": true
-				}
-			}
-		},
 		"unist-util-generated": {
 			"version": "1.1.6",
 			"resolved": "https://registry.npmjs.org/unist-util-generated/-/unist-util-generated-1.1.6.tgz",
diff --git a/package.json b/package.json
index 1fe43780ea5020..562f8860adb700 100755
--- a/package.json
+++ b/package.json
@@ -191,8 +191,8 @@
 		"node-watch": "0.7.0",
 		"npm-run-all": "4.1.5",
 		"patch-package": "6.2.2",
-		"postcss": "8.2.15",
-		"postcss-loader": "6.1.1",
+		"postcss": "8.4.5",
+		"postcss-loader": "6.2.1",
 		"prettier": "npm:wp-prettier@2.2.1-beta-1",
 		"progress": "2.0.3",
 		"react": "17.0.2",
diff --git a/packages/base-styles/_mixins.scss b/packages/base-styles/_mixins.scss
index f3e24b1f99d621..069f1b2f974285 100644
--- a/packages/base-styles/_mixins.scss
+++ b/packages/base-styles/_mixins.scss
@@ -214,16 +214,12 @@
 			transition-duration: 0s;
 			transition-delay: 0s;
 		}
-	}
-
-	@else if $property == "animation" {
+	} @else if $property == "animation" {
 		@media (prefers-reduced-motion: reduce) {
 			animation-duration: 1ms;
 			animation-delay: 0s;
 		}
-	}
-
-	@else {
+	} @else {
 		@media (prefers-reduced-motion: reduce) {
 			transition-duration: 0s;
 			transition-delay: 0s;
diff --git a/packages/block-editor/src/components/link-control/style.scss b/packages/block-editor/src/components/link-control/style.scss
index cd1174e430d73e..dc916dad5b5474 100644
--- a/packages/block-editor/src/components/link-control/style.scss
+++ b/packages/block-editor/src/components/link-control/style.scss
@@ -61,7 +61,7 @@ $preview-image-height: 140px;
 	// Specificity overide of URLInput defaults.
 	&.block-editor-url-input input[type="text"].block-editor-url-input__input {
 		@include input-control;
-		width: calc(100% - #{$grid-unit-20*2});
+		width: calc(100% - #{$grid-unit-20 * 2});
 		display: block;
 		padding: 11px $grid-unit-20;
 		padding-right: ( $button-size * $block-editor-link-control-number-of-actions ); // width of reset and submit buttons
diff --git a/packages/scripts/CHANGELOG.md b/packages/scripts/CHANGELOG.md
index 22d8077ee29db5..f234def81e886c 100644
--- a/packages/scripts/CHANGELOG.md
+++ b/packages/scripts/CHANGELOG.md
@@ -10,6 +10,7 @@
 -   The bundled `webpack-cli` dependency has been updated to the next major version `^4.9.1` ([#28273](https://github.com/WordPress/gutenberg/pull/28273)).
 -   The peer `jest` dependency has been updated from requiring `>=26` to requiring `>=27` (see [Breaking Changes](https://jestjs.io/blog/2021/05/25/jest-27), [#33287](https://github.com/WordPress/gutenberg/pull/33287)).
 -   The bundled `jest-dev-server` dependency has been updated to the next major version `^6.0.0` ([#33287](https://github.com/WordPress/gutenberg/pull/33287)).
+-   The bundled `stylelint` dependency has been updated from requiring `^13.8.0` to requiring `^14.2.0` ([#38091](https://github.com/WordPress/gutenberg/pull/38091)).
 
 ### New Features
 
diff --git a/packages/scripts/package.json b/packages/scripts/package.json
index 4b50d2c975cf99..6711ff42bc0ca4 100644
--- a/packages/scripts/package.json
+++ b/packages/scripts/package.json
@@ -72,8 +72,8 @@
 		"minimist": "^1.2.0",
 		"npm-package-json-lint": "^5.0.0",
 		"npm-packlist": "^3.0.0",
-		"postcss": "^8.2.15",
-		"postcss-loader": "^6.1.1",
+		"postcss": "^8.4.5",
+		"postcss-loader": "^6.2.1",
 		"prettier": "npm:wp-prettier@2.2.1-beta-1",
 		"puppeteer-core": "^11.0.0",
 		"react-refresh": "^0.10.0",
@@ -82,7 +82,7 @@
 		"sass": "^1.35.2",
 		"sass-loader": "^12.1.0",
 		"source-map-loader": "^3.0.0",
-		"stylelint": "^13.8.0",
+		"stylelint": "^14.2.0",
 		"terser-webpack-plugin": "^5.1.4",
 		"url-loader": "^4.1.1",
 		"webpack": "^5.47.1",
diff --git a/packages/stylelint-config/CHANGELOG.md b/packages/stylelint-config/CHANGELOG.md
index 843c4aee913cbc..e55e537468097a 100644
--- a/packages/stylelint-config/CHANGELOG.md
+++ b/packages/stylelint-config/CHANGELOG.md
@@ -2,6 +2,10 @@
 
 ## Unreleased
 
+### Breaking Change
+
+-   Increased minimum peer dependency of `stylelint` to `14.2.0` ([#38091](https://github.com/WordPress/gutenberg/pull/38091)). See [official migration guide to v14](https://github.com/stylelint/stylelint/blob/14.0.0/docs/migration-guide/to-14.md) for details.
+
 ## 19.0.0 (2021-01-21)
 
 ### Breaking Change
diff --git a/packages/stylelint-config/package.json b/packages/stylelint-config/package.json
index 1569069a0939c2..49743df11b85d5 100644
--- a/packages/stylelint-config/package.json
+++ b/packages/stylelint-config/package.json
@@ -31,12 +31,11 @@
 	],
 	"main": "index.js",
 	"dependencies": {
-		"stylelint-config-recommended": "^3.0.0",
-		"stylelint-config-recommended-scss": "^4.2.0",
-		"stylelint-scss": "^3.17.2"
+		"stylelint-config-recommended": "^6.0.0",
+		"stylelint-config-recommended-scss": "^5.0.2"
 	},
 	"peerDependencies": {
-		"stylelint": "^13.7.0 || ^14"
+		"stylelint": "^14.2"
 	},
 	"npmpackagejsonlint": {
 		"extends": "@wordpress/npm-package-json-lint-config",
diff --git a/packages/stylelint-config/test/__snapshots__/scss.js.snap b/packages/stylelint-config/test/__snapshots__/scss.js.snap
index 7b12c9a8630734..d3ca3a505b7a44 100644
--- a/packages/stylelint-config/test/__snapshots__/scss.js.snap
+++ b/packages/stylelint-config/test/__snapshots__/scss.js.snap
@@ -28,7 +28,7 @@ Array [
     "line": 1,
     "rule": "scss/at-rule-no-unknown",
     "severity": "error",
-    "text": "Unexpected unknown at-rule \\"@unknown\\" (at-rule-no-unknown) (scss/at-rule-no-unknown)",
+    "text": "Unexpected unknown at-rule \\"@unknown\\" (scss/at-rule-no-unknown)",
   },
   Object {
     "column": 2,
diff --git a/packages/stylelint-config/test/scss-valid.scss b/packages/stylelint-config/test/scss-valid.scss
index e424c7cfe37a49..a46b5d2c31ed87 100644
--- a/packages/stylelint-config/test/scss-valid.scss
+++ b/packages/stylelint-config/test/scss-valid.scss
@@ -1,4 +1,4 @@
-@import "path/to/foo.scss";
+@import "path/to/foo";
 
 @function fooBar {
 
@@ -22,8 +22,10 @@ $map: (
 	display: inline-block;
 }
 
+// stylelint-disable no-invalid-position-at-import-rule
 @import "../some/url";
 @import "../another/url";
+// stylelint-enable no-invalid-position-at-import-rule
 
 b {