Beat the cold milk, vanilla pudding, and extract until thickened in a big bowl. Condensed milk should be added, then beaten together.
Beat the heavy whipping cream until firm peaks form in a another bowl. With a spatula, carefully fold in roughly two thirds of the whipped cream into the pudding.
With a spatula, combine the remaining one-third of whipped cream with the powdered sugar. Keep chilled until required.
Place 1/4 of the vanilla wafers and 1/4 of the bananas in the bottom of your trifle basin.
Over the bananas/wafers, spread 1/4 of the pudding. Up till there are four layers, repeat with the remaining ones.
Overtop the pudding, spread the remaining whipped cream, and add any desired decorations. Two hours before serving, cover and chill the dish.