Clean the strawberries. Cut the steam side off the strawberries to make a flat surface on one side of the strawberries. This cut off the top ? off the top of each of the strawberries for the Santa hats (set aside). Pat dry the cut sides of the strawberries so that the cream cheese mixture doesn't slide off.
In a large mixing bowl, beat together the cream cheese, powdered sugar and vanilla extract.
Put the cream cheese mixture into a piping bag and pipe the mixture on top of the flat berry tops (we used a Wilton 1A tip to pipe the mixture onto the strawberries). Create a large upward swirl with the cream cheese mixture.
Gently top each strawberry with the reserved strawberry tops.
Then use the smallest piping nozzle (I used a Wilton 18 star tip) to pipe some of the cream cheese mixture on top of the strawberry hats to make the pom poms and a small amount on the front of the large strawberry pieces to make a button.
Use tweezers to gently place the mini chocolate chips into the cream cheese mixture in between each strawberry piece to make the Santa face.