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In a mixing bowl, beat the softened cream cheese and powdered sugar until smooth and creamy.
In another bowl, whip the heavy cream until soft peaks form. Gently fold the whipped cream into the cream cheese mixture.
Stir in the Baileys Irish Cream and vanilla extract until well combined.
In a trifle dish or individual cups, layer half of the crushed chocolate cookies at the bottom.
Add half of the Baileys cheesecake mixture on top of the cookies.
Follow with a layer of chocolate pudding and repeat the layers with the remaining ingredients.
Finish with a layer of whipped cream and garnish with chocolate shavings or a dusting of cocoa powder.
Refrigerate for at least 2 hours before serving to allow the flavors to meld.