Add whipping cream and vanilla extract to a large chilled mixing bowl.
Use a hand mixer (a stand mixer works too but it's more cleanup in my opinion) on a medium to high speed to beat the whipped cream until it starts to get a little thick.
Add the powdered sugar and continue to beat the whipped cream until stiff peaks* form. Do NOT continue to beat the whipped cream after you get those stiff peaks or else it will start to get lumpy and butter-like.
Put on big dollop on top of your favorite pie and enjoy! And don't forget to let you pup lick the beaters (homemade puppuccino ftw).
Notes
Storage: homemade whipped cream is best when served the same day but will keep up to 3-5 days in the fridge in an airtight container. After a few days, the whipped cream at the bottom of the container may be runny, this is normal and still fine to eat and you can easily whip it back up.