Combine 1 cup of milk and the powdered sugar in a quart-size jar. Whisk or shake to combine. Add the remaining milk, half-and-half, bourbon, and vanilla to the jar. Stir well.
Place the jar in the freezer and chill the milk punch until it is quite slushy, about 3-4 hours, shaking the jar or stirring the mixture a couple of times while it is chilling.
Once frozen into a slushy mixture, stir well and pour into glasses, top with a dash of nutmeg.
Notes
Bourbon, brandy, and whiskey are all used in Milk Punch. Feel free to use whichever one you like best. If you have it available, fresh nutmeg is always my preference for the best flavor.