Slice the strawberries and place them in a large bowl.
Sprinkle ¼ cup granulated sugar over the strawberries.
Stir gently and set aside for at least 30 minutes.
Preheat the oven to 425°F.
In a large mixing bowl, combine the flour, ¼ cup granulated sugar, baking powder, and salt.
Add the cold butter pieces to the flour mixture.
Use your fingers or a pastry cutter to blend until the mixture looks crumbly.
Pour in the milk and 1 teaspoon vanilla extract.
Stir just until combined, being careful not to overmix.
Drop large spoonfuls of dough onto a parchment-lined baking sheet, making six shortcakes.
Bake for 12 to 15 minutes or until the tops are golden brown.
Remove from the oven and let cool for about 10 minutes.
In a separate bowl, pour in the cold heavy whipping cream.
Add powdered sugar and 1 teaspoon vanilla extract.
Beat with a hand mixer until soft peaks form.
Split each shortcake in half using a fork or your hands.
Spoon strawberries and their juices onto the bottom half of each shortcake.
Add a generous layer of whipped cream.
Place the top half of the shortcake over the cream.
Add more strawberries and whipped cream on top if desired.
Serve immediately and enjoy!