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Beat whipping cream, sugar, and vanilla until soft peaks form.
Add in mascarpone cheese and amaretto (if using) and continue to whip to stiff peaks.
Dip ladyfingers in coffee (and brandy if using) and place in an 8×8 pan to make the first layer – you can fit about 7-9 cookies in each layer. Don't let them soak as the will fall apart, just a quick dunk in the coffee is enough.
Spread half of the whipped cream mixture on top of the first layer of ladyfingers. Repeat process with the second layer of ladyfingers and cream mixture.
Dust the top of dessert with cocoa powder using a sieve. Refrigerate for about 2-4 hours (it gets even better in the fridge and is a perfect make-ahead dessert).