For the Strawberry Shortcake Cookies
Combine flour, butter, 1/2 cup powdered sugar, and salt in a mixing bowl. Beat until combined. Roll dough out to 1/2-inch thickness. Using a cookie cutter (2-3 inches, mine was 2 1/2 inches), cut out cookies. Bake on parchment paper at 350 degrees F. for 20 to 22 minutes or until lightly golden. Remove from oven and allow to cool.
For the Whipped Topping
With a mixer and whisk attachment, whip heavy cream until stiff peaks form. Beat in the vanilla and 2 tablespoons powdered sugar. Whisk again until peaks form. Remove and keep refrigerated until ready to prepare strawberry shortcake stacks.
Layer a cookie with sliced strawberries, whipped topping, and repeat each layer. Top with a strawberry.