Place confectioners’ sugar into a medium bowl.
Add cream cheese and vanilla.
Mix with an electric hand mixer to create thick frosting. Add more confectioners’ sugar as needed to adjust thickness.
Transfer frosting to a piping bag fitted with a large round tip. Alternatively, use a zip-lock bag and snip off one corner to create a disposable piping bag.
Refrigerate frosting for 10-15 minutes or until firm.
Slice green tops from strawberries.
Hollow out the center of the berries carefully with a pairing knife.
Slice off the top 1/3 from the tip of the berries and reserve tips to make Santa’s hats.
Place cookies in a single layer on a serving platter or on individual dessert plates.
Place chocolate chips into a microwave-safe bowl.
Heat chocolate chips in microwave on low power for 5-10 seconds.
Stir chocolate chips. Repeat heating and stirring in short increments until chocolate is melted and completely smooth.
Dip the wide base of one strawberry into melted chocolate.
Place the dipped end of the strawberry onto one cookie to make Santa’s body.
Dip two blueberries halfway into melted chocolate.
Place dipped blueberries onto the cookie to form Santa's boots.
Pipe a large dollop of frosting on top of the body to make Santa’s head.
Pipe a small dollop of frosting onto the front of the head to make Santa’s beard.
Press one pinch of coconut into the beard.
Press one mini white chocolate chip into the face to make Santa’s nose.
Press two mini semi-sweet chocolate chips into the face to make Santa’s eyes.
Pipe frosting around the base of one strawberry tip to make trim for Santa’s hat.
Press pinches of coconut into the hat trim.
Place the hat onto Santa’s head.
Pipe a tiny dollop of frosting on top of the hat.
Sprinkle the hat with coconut.
Use a toothpick to clean up decoration details as needed.
Chill the strawberry Santa in the refrigerator.
Repeat steps with remaining ingredients to make 12 strawberry Santas.
Serve immediately or keep chilled in the refrigerator until ready to serve.