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In a large bowl, beat the cold milk with vanilla extract and vanilla pudding packets until it thickens. Pour in the condensed milk and beat to combine.
In a separate bowl, beat the heavy whipping cream until stiff peaks form. Add about two-thirds of the whipped cream into the pudding and gently fold in with a spatula.
Add the powdered sugar into the remaining one-third whipped cream and fold with a spatula to combine. Refrigerate until needed.
Add about ¼th of the vanilla wafers into the bottom of your trifle bowl and about ¼th of the bananas.
Spread ¼ of the pudding over the bananas/wafers. Repeat with the remaining layers until you have four layers.
Add the reserved whipped cream over the top of the pudding and decorate as desired. Cover and refrigerate 2 hours before serving.