In a medium bowl, whisk together the instant vanilla pudding mix and cold milk until thickened. Set aside.
In a separate bowl, beat the heavy cream, powdered sugar, and vanilla extract until soft peaks form.
Gently fold the whipped cream into the prepared pudding until smooth and creamy.
Spread a thin layer of the pudding mixture in the bottom of an 8x8 or 9x9 dish.
Add a single layer of graham crackers, breaking pieces as needed to fit.
Spread a layer of pudding mixture over the graham crackers.
Add a layer of sliced strawberries.
Repeat the layers, ending with pudding mixture and strawberries on top.
Cover and refrigerate for at least 4 hours, or overnight for the best texture.
Slice and serve chilled.