Place cream cheese, vanilla extract, and confectioners’ sugar into a medium bowl. Mix until creamy.
Add heavy cream and mix until the mixture is thick, smooth, and creamy. 4-5 minutes.
Transfer the frosting to a piping bag.
Prepare the strawberries by carefully washing them. Make sure they are dry so the filling doesn't just slip off the berry.
Cut the stem off each strawberry then cut 1/4 off the top of each strawberry to create a smaller cone for Santa’s hat. Set the Santa hats aside.
Pipe the cream cheese mixture onto the bottom parts of the larger strawberry pieces. To create Santa's beard.
Add the top strawberry piece or Santa hat on top of the body.
You can dust powdered sugar over the hat to give it that snowy look or you can leave it as it is. Then use the piping bag to add the white pom-pom hat top.
To create Santa's mustache pipe 2 side swirls.
Add 2 mini chocolate chip pieces for the eyes. Refrigerate until ready to serve. Enjoy!