Crush the Oreos by placing them in a resealable plastic bag and using a rolling pin or your hands to crush them into small pieces, leaving a few larger chunks for crunch.

In a blender, add the crushed Oreos, vanilla ice cream, and milk, then blend on high speed until smooth and creamy.

Adjust the consistency by adding more milk as desired.

Once blended, stir the milkshake with a spoon to ensure any larger cookie pieces are mixed in.

Pour the milkshake into tall glasses, top with whipped cream and extra crushed Oreos if desired, then serve immediately.