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.

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.