Start by baking the gingerbread cake according to the package instructions. Once baked, let it cool completely so it doesn’t melt the creamy layers later. Cut the cake into bite-sized cubes to make layering easy and neat.
In a bowl, whisk together the instant pudding mix and cold milk until thick and smooth. Let it sit for a few minutes so it fully sets. This creamy layer adds richness and balances the spice of the gingerbread.
Beat the cream cheese with powdered sugar until smooth. Slowly add heavy cream and vanilla extract, then whip until stiff peaks form. Reserve a portion of this whipped cream for decorating the top later.
Divide the remaining whipped cream into two bowls. Gently fold one portion into the pudding and the other into the dulce de leche. Folding instead of stirring keeps the mixtures light and fluffy.
Place half of the gingerbread cubes into the bottom of the trifle dish. Spread a layer of vanilla cream, followed by a layer of dulce de leche cream. Sprinkle crushed cookies over the cream. Repeat the layers with remaining ingredients.
Cover the trifle and refrigerate for at least two hours so the flavors meld together. Before serving, pipe the reserved whipped cream on top and garnish with whole gingerbread cookies for a festive finish.