Line an 8×8-inch square tin with parchment, clingfilm/plastic wrap, or aluminum foil, allowing a 2-inch overhang on all sides. (See notes.)

Place 14 of the Oreos in a large plastic food storage bag, and use a kitchen mallet to crush. Set aside.

In a large mixing bowl or the bowl of a stand mixer, whip the cream until soft peaks form. Mix in the confectioner’s sugar and vanilla bean paste.

Divide whipped cream into two equal portions.

With a rubber spatula, fold about 2/3 of the crushed Oreos into one portion of whipped cream. Refrigerate until ready to use.

With a small stepped palette knife, spread a thin layer of the plain whipped cream across bottom of prepared tin.

Arrange a layer of Oreos on top of the cream. You should have 4 rows of 4, or 16 total.

With a small stepped palette knife or rubber spatula, spread chocolate pudding on top of the Oreos, completely covering the cookies.

Top pudding with a second layer of Oreos.

With a small stepped palette knife or rubber spatula, spread Oreo whipped cream on top of the second Oreo layer, completely covering the cookies.

Top Oreo whipped cream with a third layer of Oreos.

Spread with the remaining plain whipped cream, using a small stepped palette knife to create swirls and peaks in the cream.

Sprinkle with remaining crushed Oreos.

Cover pan loosely with foil, creating a tent shape so it does not touch the cream directly. Refrigerate at least 8 hours, or overnight.

With a sharp chef’s knife, slice icebox cake into squares. Serve accompanied by whole or halved Oreos, fresh berries, or sprigs of fresh mint.

Store leftover icebox cake in the refrigerator for up to 2 days.