Add the strawberries to a medium mixing bowl. Pour in the granulated sugar, stir, and let sit to macerate for 15 to 30 minutes.
In a stand mixer, whisk the heavy cream, powdered sugar, and vanilla on medium speed until it reaches stiff peaks. Set aside.
Prepare the vanilla pudding according to the package directions. Set aside.
Cut the angel food cake into 1-inch cubes. Set aside.
Assembly
Add half of the angel food cake cubes to the bottom of a trifle bowl in an even layer. Top the cake with 1/3 of the berries. Spread half of the pudding over the berries and then top with half of the whipped cream, spreading it all the way to the edges.
Repeat the layers once again. Finish the trifle by topping it with the remaining berries and a sprig of mint and/or a whole strawberry.
Keep chilled until ready to serve.
Notes
If you can't find a large box of pudding mix, you can use two of the smaller 3-ounce boxes and 3 cups of milk instead. The pudding will be on the thicker side.