In a medium bowl, add the powdered sugar and heavy whipping cream.
Whisk together until stiff peaks form.
Add the peppermint extract and whisk in to the whipped cream until combined.
Assemble your trifle.
Layer in this order: 1/2 the brownies, 1/2 the whipped cream, gingerbread cookies laid flat, 1 cup chocolate pudding, gingerbread cookies laid flat, the remaining pudding, the remaining brownies, the remaining whipped cream.
Sprinkle the crushed candy cane on top and refrigerate until ready to serve.