In the bowl of an electric mixer fitted with a whisk attachment, combine heavy cream, mascarpone, sugar, coffee liqueur, cocoa powder, espresso powder and vanilla. Mix on low speed to combine and then slowly raise sped until it forms firm peaks.
To assemble the cake, arrange chocolate chip cookies flat in an 8" springform pan, covering bottom as much as possible.
Break cookies to fill in the spaces. Spread a fifth of the mocha whipped cream over the cookies.
Place another layer of cookies on top,lying flat and touching, followed by another 1/5 of the cream. Continue layering cookies and cream until there are 5 layers of each, ending with a layer of cream.
Smooth the top, cover with plastic wrap and refrigerate overnight. Run a small sharp knife around the outside of the cake and remove the sides of the pan. Sprinkle the top with chocolate shavings, cut in wedges and serve cold.