01 - Add the strawberries, Oreo cookies, vanilla ice cream, and whole milk to a blender.
02 - Blend on high until the mixture is completely smooth and creamy with no large cookie chunks remaining.
03 - Taste the shake and add more milk in small increments if a thinner consistency is preferred.
04 - Divide the milkshake evenly between two chilled glasses.
05 - Top each glass with whipped cream, crushed Oreo pieces, and fresh strawberry slices. Serve immediately.