Place the Oreo cookies in a large, resealable plastic bag. Using a rolling pin or similar utensil, crush the cookies into a mixture of crumbs and small pieces. Set aside.

In a large mixing bowl, beat the softened cream cheese using an electric hand mixer set to medium speed until smooth and creamy. Scrape down the sides of the bowl. Gradually add the powdered sugar, ¼ cup at a time, mixing on low speed until fully incorporated.

Add the vanilla extract to the cream cheese mixture. Beat again briefly until combined and the mixture appears light and fluffy.

Using a rubber spatula, gently fold the thawed Cool Whip into the cream cheese mixture. Continue folding until the mixture is well blended and smooth.

Add the crushed Oreo cookies to the bowl and fold them in gently until they are evenly distributed throughout the dip.

Transfer the Oreo dip to a serving bowl. If not serving immediately, cover the bowl tightly with plastic wrap and refrigerate for at least 1 hour to allow the flavors to meld and the texture to firm slightly.

When ready to serve, garnish the top of the dip with additional crushed Oreos if desired. Serve with your choice of dippers such as graham crackers, pretzels, vanilla wafers, apple slices, or fresh strawberries.