In a large mixing bowl, whisk together the milk and the instant chocolate pudding mix for about two minutes. Once the mixture starts to thicken, set it aside in the refrigerator for at least five minutes to firm up completely. Using cold milk will help the pudding set faster and create a smoother texture for your cups.
In a separate chilled bowl, beat the heavy whipping cream, powdered sugar, and alcohol-free vanilla until stiff peaks form. You want the cream to be firm enough to hold the weight of a strawberry without collapsing. Transfer about half of the whipped cream into a piping bag fitted with a large round or star tip for the assembly phase.
Wash the strawberries and pat them completely dry with a paper towel. Remove the green leafy stems by cutting a flat base across the top of each berry. This flat surface will allow the strawberry “hat” to sit securely on top of the pudding and cream layers.
Spoon the chilled chocolate pudding evenly into six small clear glass cups or ramekins. Smooth the tops with the back of a spoon to create an even surface. If you want a cleaner look, you can also pipe the pudding into the cups using a large plastic bag with the corner snipped off.
Pipe a thick ring of whipped cream around the top edge of each pudding cup to represent the fur trim of the hat. Place a strawberry, cut side down, into the center of the whipped cream ring. Finally, pipe a small dot of whipped cream or place a mini marshmallow on the tip of the strawberry to finish the Santa hat look.
