Whisk dry ingredients: In a bowl, whisk flour, cornstarch, baking powder, and salt. Set aside.
Cream butter and sugar: In a large bowl, beat softened butter and sugar until light and fluffy, about 2–3 minutes.
Add egg and extracts: Mix in the egg, vanilla, and almond extract (if using) until smooth.
Bring dough together: Add dry ingredients in two additions.
Mix just until combined and the dough holds together. Do not overmix.
Chill: Divide dough in half, flatten into discs, wrap, and chill for at least 1 hour (or up to 2 days). Chilled dough = clean shapes.
Preheat and prep: Heat oven to 350°F (175°C). Line baking sheets with parchment.
Roll and cut: On a lightly floured surface, roll dough to about 1/4 inch thick.
Use an oval cutter, or cut ovals by hand. Gently pinch one end to form a football shape if needed.
Bake: Place cookies 2 inches apart and bake 9–11 minutes, until edges are just turning golden. Do not overbake for soft centers.
Cool: Let cookies rest on the sheet 5 minutes, then transfer to a rack to cool completely before icing.
Make icing: Whisk powdered sugar, milk, vanilla, and a pinch of salt until smooth. You want a pipeable but not runny consistency—like school glue.
Divide: tint most of it brown, leave some white for the laces.
Decorate: Outline and fill each cookie with brown icing. Let set 15–30 minutes. Pipe one white horizontal stripe near each end, plus one center line and short cross-laces.
Let dry until set.