diff --git a/packages/alfa-css/src/value/percentage.ts b/packages/alfa-css/src/value/percentage.ts
index dfde39d0cc..e64fdc9c4c 100644
--- a/packages/alfa-css/src/value/percentage.ts
+++ b/packages/alfa-css/src/value/percentage.ts
@@ -33,7 +33,7 @@ export class Percentage extends Numeric<"percentage"> {
   }
 
   public toString(): string {
-    return `${this._value}%`;
+    return `${this._value * 100}%`;
   }
 }
 
diff --git a/packages/alfa-style/src/property.ts b/packages/alfa-style/src/property.ts
index 5c0a2b6345..90a1d3fcff 100644
--- a/packages/alfa-style/src/property.ts
+++ b/packages/alfa-style/src/property.ts
@@ -219,6 +219,7 @@ const Longhands = {
   display: Display,
   "font-family": Font.Family,
   "font-size": Font.Size,
+  "font-stretch": Font.Stretch,
   "font-style": Font.Style,
   "font-weight": Font.Weight,
   height: Height,
@@ -258,6 +259,7 @@ const Shorthands = {
   background: Background.Shorthand,
   "background-repeat": Background.Repeat.Shorthand,
   "background-position": Background.Position.Shorthand,
+  font: Font.Shorthand,
   "inset-block": Inset.Block.Shorthand,
   "inset-line": Inset.Line.Shorthand,
   outline: Outline.Shorthand,
diff --git a/packages/alfa-style/src/property/box-insets.ts b/packages/alfa-style/src/property/box-insets.ts
index d748f7350d..6f3d17d83a 100644
--- a/packages/alfa-style/src/property/box-insets.ts
+++ b/packages/alfa-style/src/property/box-insets.ts
@@ -4,7 +4,7 @@ import { Parser } from "@siteimprove/alfa-parser";
 import { Property } from "../property";
 import { Resolver } from "../resolver";
 
-const { either, map, oneOrMore, separatedList } = Parser;
+const { either, map, separatedList } = Parser;
 
 /**
  * @see https://drafts.csswg.org/css-position/#insets
@@ -67,17 +67,14 @@ export namespace Inset {
      */
     export const Shorthand = Property.Shorthand.of(
       ["inset-block-start", "inset-block-end"],
-      map(
-        separatedList(parseInset, Token.parseWhitespace),
-        (values) => {
-          const [start, end] = [...values];
-
-          return [
-            ["inset-block-start", start],
-            ["inset-block-end", end ?? start],
-          ];
-        }
-      )
+      map(separatedList(parseInset, Token.parseWhitespace), (values) => {
+        const [start, end] = [...values];
+
+        return [
+          ["inset-block-start", start],
+          ["inset-block-end", end ?? start],
+        ];
+      })
     );
   }
 
@@ -91,17 +88,14 @@ export namespace Inset {
      */
     export const Shorthand = Property.Shorthand.of(
       ["inset-line-start", "inset-line-end"],
-      map(
-        separatedList(parseInset, Token.parseWhitespace),
-        (values) => {
-          const [start, end] = [...values];
-
-          return [
-            ["inset-line-start", start],
-            ["inset-line-end", end ?? start],
-          ];
-        }
-      )
+      map(separatedList(parseInset, Token.parseWhitespace), (values) => {
+        const [start, end] = [...values];
+
+        return [
+          ["inset-line-start", start],
+          ["inset-line-end", end ?? start],
+        ];
+      })
     );
   }
 }
diff --git a/packages/alfa-style/src/property/font.ts b/packages/alfa-style/src/property/font.ts
index 571ebc0a5e..86f00025f8 100644
--- a/packages/alfa-style/src/property/font.ts
+++ b/packages/alfa-style/src/property/font.ts
@@ -6,22 +6,38 @@ import {
   Calculation,
   String,
   Number,
+  Angle,
 } from "@siteimprove/alfa-css";
 import { Parser } from "@siteimprove/alfa-parser";
+import { Result } from "@siteimprove/alfa-result";
 import { Slice } from "@siteimprove/alfa-slice";
 
 import { Property } from "../property";
 import { Resolver } from "../resolver";
 
-const { map, filter, either, option, delimited, separatedList } = Parser;
+import { Line } from "./line";
+
+const {
+  delimited,
+  either,
+  filter,
+  map,
+  option,
+  pair,
+  right,
+  separatedList,
+} = Parser;
 
 export namespace Font {
   export type Family = Family.Specified;
 
   export namespace Family {
-    export type Generic = Keyword<
-      "serif" | "sans-serif" | "cursive" | "fantasy" | "monospace"
-    >;
+    export type Generic =
+      | Keyword<"serif">
+      | Keyword<"sans-serif">
+      | Keyword<"cursive">
+      | Keyword<"fantasy">
+      | Keyword<"monospace">;
 
     export type Specified = Array<Generic | String>;
   }
@@ -56,18 +72,17 @@ export namespace Font {
   export type Size = Size.Specified | Size.Computed;
 
   export namespace Size {
-    export type Absolute = Keyword<
-      | "xx-small"
-      | "x-small"
-      | "small"
-      | "medium"
-      | "large"
-      | "x-large"
-      | "xx-large"
-      | "xxx-large"
-    >;
-
-    export type Relative = Keyword<"larger" | "smaller">;
+    export type Absolute =
+      | Keyword<"xx-small">
+      | Keyword<"x-small">
+      | Keyword<"small">
+      | Keyword<"medium">
+      | Keyword<"large">
+      | Keyword<"x-large">
+      | Keyword<"xx-large">
+      | Keyword<"xxx-large">;
+
+    export type Relative = Keyword<"larger"> | Keyword<"smaller">;
 
     export type Specified =
       | Absolute
@@ -198,10 +213,84 @@ export namespace Font {
     }
   );
 
-  export type Style = Keyword<"normal" | "italic" | "oblique">;
+  export namespace Stretch {
+    export type Absolute =
+      | Keyword<"ultra-condensed">
+      | Keyword<"extra-condensed">
+      | Keyword<"condensed">
+      | Keyword<"semi-condensed">
+      | Keyword<"normal">
+      | Keyword<"semi-expanded">
+      | Keyword<"expanded">
+      | Keyword<"extra-expanded">
+      | Keyword<"ultra-expanded">;
+
+    export type Specified = Absolute | Percentage;
+
+    export type Computed = Percentage;
+  }
+
+  /**
+   * @see https://drafts.csswg.org/css-fonts/#font-stretch-prop
+   */
+  export const Stretch: Property<
+    Stretch.Specified,
+    Stretch.Computed
+  > = Property.of(
+    Percentage.of(1),
+    either(
+      Percentage.parse,
+      Keyword.parse(
+        "ultra-condensed",
+        "extra-condensed",
+        "condensed",
+        "semi-condensed",
+        "normal",
+        "semi-expanded",
+        "expanded",
+        "extra-expanded",
+        "ultra-expanded"
+      )
+    ),
+    (style) =>
+      style.specified("font-stretch").map((stretch) => {
+        if (stretch.type === "percentage") {
+          return stretch;
+        }
+
+        switch (stretch.value) {
+          case "ultra-condensed":
+            return Percentage.of(0.5);
+          case "extra-condensed":
+            return Percentage.of(0.625);
+          case "condensed":
+            return Percentage.of(0.75);
+          case "semi-condensed":
+            return Percentage.of(0.875);
+          case "normal":
+            return Percentage.of(1);
+          case "semi-expanded":
+            return Percentage.of(1.125);
+          case "expanded":
+            return Percentage.of(1.25);
+          case "extra-expanded":
+            return Percentage.of(1.5);
+          case "ultra-expanded":
+            return Percentage.of(2);
+        }
+      }),
+    { inherits: true }
+  );
+
+  export type Style =
+    | Keyword<"normal">
+    | Keyword<"italic">
+    | Keyword<"oblique">;
 
   /**
    * @see https://drafts.csswg.org/css-fonts/#font-style-prop
+   *
+   * oblique accepting an angle has poor browser support and shouldn't affect Alfa currently.
    */
   export const Style: Property<Style> = Property.of(
     Keyword.of("normal"),
@@ -215,9 +304,9 @@ export namespace Font {
   export type Weight = Weight.Specified | Weight.Computed;
 
   export namespace Weight {
-    export type Absolute = Keyword<"normal" | "bold">;
+    export type Absolute = Keyword<"normal"> | Keyword<"bold">;
 
-    export type Relative = Keyword<"bolder" | "lighter">;
+    export type Relative = Keyword<"bolder"> | Keyword<"lighter">;
 
     export type Specified = Absolute | Relative | Number;
 
@@ -287,4 +376,139 @@ export namespace Font {
       inherits: true,
     }
   );
+
+  /**
+   * Parses the "combinator any" part of the font shorthand.
+   */
+  const parseFontAny: Parser<
+    Slice<Token>,
+    [
+      ["font-stretch", Stretch.Specified],
+      ["font-style", Style],
+      ["font-weight", Weight.Specified]
+    ],
+    string
+  > = (input) => {
+    const normal = Keyword.of("normal");
+
+    // "normal" can be a keyword for each of these four longhands, making parsing annoying…
+    // Fortunately, "normal" happens to also be the initial value of these longhands.
+    // So, we can have them default to "normal", and try to overwrite them as long as they still are "normal";
+    // when "normal" keyword is encountered, it will be affected to the first still "normal" longhand (for no effect)
+    // and the end result is OK (only the longhands with a non-"normal" specified value are changed).
+    //
+    // This approach will stop working if CSS ever decides that the initial value of these longhands is not "normal"
+    // or that setting the shorthand does not reset all the longhands. Both seem to be unlikely changes.
+    // It is nonetheless hacky to hardcode the initial value instead of using Keyword.of("initial") in the end…
+    let stretch: Stretch.Specified = normal;
+    let style: Style = normal;
+    let variant: Keyword<"normal"> | Keyword<"small-caps"> = normal;
+    let weight: Weight.Specified = normal;
+
+    while (true) {
+      for (const [remainder] of Token.parseWhitespace(input)) {
+        input = remainder;
+      }
+
+      if (normal.equals(stretch)) {
+        // only keyword stretch are allowed in the shorthand
+        const result = Keyword.parse(
+          "ultra-condensed",
+          "extra-condensed",
+          "condensed",
+          "semi-condensed",
+          "normal",
+          "semi-expanded",
+          "expanded",
+          "extra-expanded",
+          "ultra-expanded"
+        )(input);
+
+        if (result.isOk()) {
+          [input, stretch] = result.get();
+          continue;
+        }
+      }
+
+      if (normal.equals(style)) {
+        const result = Style.parse(input);
+
+        if (result.isOk()) {
+          [input, style] = result.get();
+          continue;
+        }
+      }
+
+      if (normal.equals(variant)) {
+        const result = Keyword.parse("normal", "small-caps")(input);
+
+        if (result.isOk()) {
+          [input, variant] = result.get();
+          continue;
+        }
+      }
+
+      if (normal.equals(weight)) {
+        const result = Weight.parse(input);
+
+        if (result.isOk()) {
+          [input, weight] = result.get();
+          continue;
+        }
+      }
+
+      break;
+    }
+
+    return Result.of([
+      input,
+      [
+        ["font-stretch", stretch],
+        ["font-style", style],
+        // we currently do not support font-variant and just ditch it.
+        ["font-weight", weight],
+      ],
+    ]);
+  };
+
+  /**
+   * Alfa is not really equipped to deal with system fonts right now.
+   * The resulting family and size depends both on the OS and on the browser.
+   */
+  export const Shorthand = Property.Shorthand.of(
+    [
+      "font-family",
+      "font-size",
+      "font-stretch",
+      "font-style",
+      "font-weight",
+      "line-height",
+    ],
+    map(
+      pair(
+        parseFontAny,
+        pair(
+          right(option(Token.parseWhitespace), Size.parse),
+          pair(
+            option(
+              right(
+                pair(
+                  pair(option(Token.parseWhitespace), Token.parseDelim("/")),
+                  option(Token.parseWhitespace)
+                ),
+                Line.Height.parse
+              )
+            ),
+            right(Token.parseWhitespace, Family.parse)
+          )
+        )
+      ),
+      ([fontAny, [size, [lineHeight, family]]]) => [
+        ...fontAny,
+        ["font-size", size],
+        ["line-height", lineHeight.getOr(Keyword.of("initial"))],
+        ["font-family", family],
+      ]
+    )
+  );
 }
diff --git a/packages/alfa-style/test/property/font.spec.tsx b/packages/alfa-style/test/property/font.spec.tsx
index 9024b9faf5..3eb0b6cbaf 100644
--- a/packages/alfa-style/test/property/font.spec.tsx
+++ b/packages/alfa-style/test/property/font.spec.tsx
@@ -6,10 +6,12 @@ import { Device } from "@siteimprove/alfa-device";
 
 import { Style } from "../../src/style";
 
+const device = Device.standard();
+
 test("#cascaded() parses `font-size: calc(1em + 2px)`", (t) => {
   const element = <div style={{ fontSize: "calc(1em + 2px)" }}></div>;
 
-  const style = Style.from(element, Device.standard());
+  const style = Style.from(element, device);
 
   t.deepEqual(style.cascaded("font-size").get().toJSON(), {
     value: {
@@ -43,7 +45,7 @@ test("#cascaded() parses `font-size: calc(1em + 2px)`", (t) => {
 test("#computed() resolves `font-size: calc(1em + 2px)`", (t) => {
   const element = <div style={{ fontSize: "calc(1em + 2px)" }}></div>;
 
-  const style = Style.from(element, Device.standard());
+  const style = Style.from(element, device);
 
   t.deepEqual(style.computed("font-size").toJSON(), {
     value: {
@@ -58,7 +60,7 @@ test("#computed() resolves `font-size: calc(1em + 2px)`", (t) => {
 test("#cascaded() parses `font-size: calc(1em + 2%)`", (t) => {
   const element = <div style={{ fontSize: "calc(1em + 2%)" }}></div>;
 
-  const style = Style.from(element, Device.standard());
+  const style = Style.from(element, device);
 
   t.deepEqual(style.cascaded("font-size").get().toJSON(), {
     value: {
@@ -91,7 +93,7 @@ test("#cascaded() parses `font-size: calc(1em + 2%)`", (t) => {
 test("#computed() resolves `font-size: calc(1em + 2%)`", (t) => {
   const element = <div style={{ fontSize: "calc(1em + 2%)" }}></div>;
 
-  const style = Style.from(element, Device.standard());
+  const style = Style.from(element, device);
 
   t.deepEqual(style.computed("font-size").toJSON(), {
     value: {
@@ -106,7 +108,101 @@ test("#computed() resolves `font-size: calc(1em + 2%)`", (t) => {
 test("#cascaded() ignores `font-size: calc(20deg)`", (t) => {
   const element = <div style={{ fontSize: "calc(20deg)" }}></div>;
 
-  const style = Style.from(element, Device.standard());
+  const style = Style.from(element, device);
 
   t.equal(style.cascaded("font-size").isNone(), true);
 });
+
+test("#cascaded() parses `font: 16px sans-serif`", (t) => {
+  const element = <div style={{ font: "16px sans-serif" }}></div>;
+
+  const style = Style.from(element, device);
+
+  t.deepEqual(style.cascaded("font-size").get().value.toJSON(), {
+    type: "length",
+    value: 16,
+    unit: "px",
+  });
+
+  t.deepEqual(style.cascaded("font-family").get().toJSON().value, [
+    {
+      type: "keyword",
+      value: "sans-serif",
+    },
+  ]);
+});
+
+test("#cascaded() assigns percentage to font-size, not font-stretch", (t) => {
+  const element = <div style={{ font: "80% sans-serif" }}></div>;
+
+  const style = Style.from(element, device);
+
+  t.deepEqual(style.cascaded("font-size").get().value.toJSON(), {
+    type: "percentage",
+    value: 0.8,
+  });
+});
+
+test("#cascaded() correctly handles line-height and font-family stack", (t) => {
+  const element = (
+    <div style={{ font: "x-large/110% 'new century schoolbook', serif" }}></div>
+  );
+
+  const style = Style.from(element, device);
+
+  t.deepEqual(style.cascaded("font-size").get().value.toJSON(), {
+    type: "keyword",
+    value: "x-large",
+  });
+
+  t.deepEqual(style.cascaded("line-height").get().value.toJSON(), {
+    type: "percentage",
+    value: 1.1,
+  });
+
+  t.deepEqual(style.cascaded("font-family").get().toJSON().value, [
+    {
+      type: "string",
+      value: "new century schoolbook",
+    },
+    { type: "keyword", value: "serif" },
+  ]);
+});
+
+test("#cascaded parses `condensed oblique753 12pt 'Helvetica Neue', serif`", (t) => {
+  const element = (
+    <div
+      style={{
+        font: "condensed oblique 753 12pt 'Helvetica Neue', serif",
+      }}
+    ></div>
+  );
+
+  const style = Style.from(element, device);
+
+  t.deepEqual(style.cascaded("font-style").get().value.toJSON(), {
+    type: "keyword",
+    value: "oblique",
+  });
+
+  t.deepEqual(style.cascaded("font-weight").get().value.toJSON(), {
+    type: "number",
+    value: 753,
+  });
+
+  t.deepEqual(style.cascaded("font-stretch").get().value.toJSON(), {
+    type: "keyword",
+    value: "condensed",
+  });
+
+  t.deepEqual(style.cascaded("font-size").get().value.toJSON(), {
+    type: "length",
+    value: 12,
+    unit: "pt",
+  });
+
+  t.deepEqual(style.cascaded("font-family").get().toJSON().value, [
+    { type: "string", value: "Helvetica Neue" },
+    { type: "keyword", value: "serif" },
+  ]);
+});