With a stand mixer or in a large bowl with a hand mixer, whisk heavy whipping cream, powdered sugar, and vanilla until stiff peaks form. Set aside.
In a large mixing bowl, whisk together powdered pudding mix, milk and condensed milk until smooth. Let sit for 3 minutes. Fold in whipped cream until smooth (reserve a little whip cream for decoration on top if desired).
In a large trifle bowl (or individual parfait glasses) assemble the pudding. First, lay one third of vanilla wafers across the bottom of the bowl. Top with one third of the banana slices. Cover with one third of the pudding mixture. Continue with two more layers, reserving a few vanilla wafers to lay across the top as garnish.
Cover pudding and let it rest in the fridge for at least 2 hours before serving. Can also be made up to a day ahead and stored in the fridge until ready to serve!