In a medium sauce pan over medium heat, add strawberries and sugar. Simmer for about 5 minutes, until strawberries are very soft. Let cool slightly, then blend with an immersion or stand blender. Set aside to cool completely.
In a blender, add ice, milk, vanilla extract, and powdered sugar. Blend until smooth. In a large glass, layer about ¼ cup of blended milk, then top with 1-2 tablespoons of strawberry sauce (depending on desired amount of strawberry flavor). Continue to layer, then top with whipped cream, if desired. Using a straw, gently stir to swirl layers together a bit (or stir more if you prefer a more homogenous drink).
Recipe by Wright Family Table at https://www.wrightfamilytable.com/iced-strawberry-creme-frappuccino-drink/