Blend 1 cup of hulled strawberries and 1/4 cup of cranberry juice with 1/2 cup of ice cubes until smooth. Divide evenly among 4 glasses to form the red base layer. Place glasses in the freezer for 10 minutes to set slightly.
Rinse the blender. Blend 1 cup of vanilla yogurt, 1/4 cup of milk, and 1/2 cup of ice cubes until smooth. Carefully pour or spoon this white mixture over the red layer. Return glasses to the freezer for 10 minutes.
Rinse the blender again. Blend the remaining 1 cup of vanilla yogurt, 1/4 cup of milk, 1/4 tsp blue food coloring, and 1 cup of ice cubes until smooth and brightly blue. Gently layer this over the white layer.
Top each glass with a generous dollop (divided from 1/2 cup total) of whipped cream.
Garnish with 1 tbsp red, white, and blue sprinkles, 1/4 cup fresh blueberries, and 1 star-shaped sugar cookie on the rim of each glass. Serve immediately.