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