Start off with adding pudding mix to a bowl along with the milk.
Using a whisk, whisk the contents until the pudding starts to thicken. Set the bowl aside.
Using a separate bowl add heavy cream. Whip the heavy cream using a handheld mixer. Whip until the consistency changes slightly. Add powdered sugar, vanilla extract, and whip on medium-high speed, until the cream forms a peak.
Using a baking dish add vanilla wafers and layer with sliced bananas. Add vanilla pudding, whip cream, and spread evenly. Top with crumbled vanilla wafer and a drizzle of caramel sauce.