Wash and cut your strawberries into quarters (reserve a few strawberries to cut in half for garnish if desired). Place in a medium sized bowl. Zest the orange and reserve for later, you will need about 1 1/2 teaspoons of zest. Juice the orange and add to the strawberries. Gently toss the strawberries and orange juice, set aside.
WHIPPED CREAM:
In a large bowl whip the cream, powdered sugar and vanilla together just until stiff peaks form. Gently fold in the reserved 1 1/2 teaspoons of orange zest, set aside. Cube the angel food in to small bite sized pieces.
ASSEMBLY:
First gently toss the strawberries in the juice one more time. Now, place a small amount of angel food in the bottom of a cup. Top with a few strawberries (don't be afraid to get some of the orange juice in there as well) then whipped cream. Repeat layers one more time. Repeat for remaining cups. Top with a strawberry half and mint leaf if desired. Refrigerate until ready to serve.
Notes
*UPDATE* I have made these 24 hours in advance when strawberries were in the off season. However, when strawberries are really ripe they will produce too much juice to make that far in advance.