Take a small bowl. Add the cream cheese and powdered sugar. Mix until well-combined. Gently stir in the whipped cream.
Use a spoon to transfer the mixture into a small resealable plastic bag. Seal the bag.
Make a hole in one corner of the bag to use as a piping bag. Pipe the cream cheese mixture on the Oreo Cookies.
Top with strawberries, bottom facing up. Gently press the top end of each strawberry into the cream cheese icing to make it firm.
Pipe the remaining cream cheese mixture onto the bottom tips of the berries.
Oreo Santa Hat Cookies are ready!