Add heavy whipping cream and powdered sugar to the bowl of a stand mixer or hand mixer with whisk attachment. Use the whisk attachment, and beat on low speed for 2-3 minutes until the sugar has dissolved and is incorporated into the heavy cream.
Next, increase the speed to medium for an additional 5-7 minutes or until the whipped cream begins to form soft peaks. Turn off the mixer.
Pour in the bourbon and vanilla, and continue to mix another 1-3 minutes until stiff peaks form.
Serve immediately, and store any leftover whipped cream in the refrigerator for up to 3 days.