9. Cindy Crawford: Leather Isn't Age Appropriate
Leather minis, dresses, and pants are meant to be earmarked for the younger generations, but Cindy Crawford proves that the fabric is open to all ages. You may be thinking, "but she's a supermodel," and it's true that she can pull off a lot of styles. But the reason she can isn't so much because of her iconic status, but because she has confidence while wearing it. If you love an outfit and feel happy while wearing it, then you can 100 percent pull it off.