In a mixing bowl, pour 2 cups of heavy whipping cream and whip at medium speed. Gradually add in ½ cup of powdered sugar until soft peaks form (about 3–5 minutes). Set aside.

In a 9x13-inch serving dish, create the first layer by placing a single layer of chocolate sandwich cookies on the bottom. Optionally dip each cookie in milk for added softness.

Spread half of the peppermint whipped cream over the cookies. Smooth the cream evenly, letting it seep slightly between the cookies.

Repeat by placing another layer of cookies on top of the whipped cream, then spoon the remaining whipped cream on top and spread to cover all cookies.

Cover the dish and refrigerate for at least 8 hours or overnight to allow flavors to meld and cookies to soften.

Before serving, sprinkle crushed peppermint candy on top. Optionally, add chocolate shavings for garnish. Cut into squares and serve chilled.