Place the vanilla ice cream, milk and cookies in a blender. Puree until smooth.
Drizzle chocolate syrup on the inside of each glass.
Pour the ice cream mixture evenly into each glass.
Top with whipped cream, a drizzle of chocolate syrup and crushed Oreos®.
Serve immediately.
Diva’s Tip: Chill your glasses in the freezer a head of time to get them nice and frosty.