Combine vanilla ice cream, milk, instant espresso powder, peppermint schnapps, coffee liqueur, Baileys Irish Cream, and chocolate syrup in a blender. Blend on high until smooth and frothy, about 30 seconds.
Drizzle extra chocolate syrup around the inside of a chilled glass so it clings to the sides, then pour in the blended cocktail.
Top with whipped cream, more chocolate syrup, and a sprinkle of crushed candy cane. Serve immediately.
Notes
If you prefer a non-alcoholic version, replace the schnapps and liqueurs with extra milk and a drop of peppermint extract.Chilling your glasses for a few minutes keeps the cocktail icy cold longer.