Add the cold heavy whipping cream, powdered sugar, and vanilla extract to a medium mixing bowl or to the bowl of your stand mixer.
2 cups heavy whipping cream or heavy cream, ¼ cup powdered sugar, 1 tsp vanilla extract
Beat on the highest speed, which is a 7 for the KitchenAid hand mixer I use, until the cream has doubled in size (typically about 2-2½ minutes for me) or until it reaches your desired consistency. I prefer when the whipped cream creates soft peaks that hold their shape but bend easily. Be careful not to overwhip the cream as it could turn to butter. Halfway through, taste the whipped cream for sweetness and add more sugar if you'd like.
Serve the whipped cream right away on your favorite pies, cakes, and other desserts. Store any leftover whipped cream in an airtight container in the fridge. Since this whipped cream does not contain stabilizers commonly found in store-bought varieties, use any leftovers within 1-2 days.