Ann Margret in Bye Bye Birdie. Duh. Who doesn't want to be Anne Margret circa Bye Bye Birdie? Obviously the yellow dress worn up against that blue screen background is iconic, but this is my favorite look from that movie. Big sweater, cuffed jeans (so ahead of your time, Ann), argyle socks and a cute cap. Comfy, sporty, American. Love it. Plus, that sweater was so big she could hide in it like a turtle if she felt threatened. Bonus.