In a large mixing bowl, whisk together the instant vanilla pudding mix and cold milk until smooth. Let it sit for about 5 minutes to thicken.
In a separate bowl, beat the heavy cream, powdered sugar, and vanilla extract until stiff peaks form.
Gently fold the whipped cream into the pudding mixture until fully combined.
In a serving dish or individual cups, layer half of the sliced bananas at the bottom.
Spoon half of the pudding mixture over the bananas, followed by half of the crushed Biscoff cookies.
Repeat the layers with the remaining bananas, pudding, and crushed cookies.
Cover and refrigerate for at least 2 hours before serving to allow the flavors to meld.
Just before serving, garnish with extra Biscoff cookies on top.