Jacky O'Shaughnessy
Jacky was launched into fame with her stunning American Apparel ads and continued to take on the fashion industry with runway walks for designers like Tome.

Age: 64

Words of wisdom: "I'm comfortable. I don't feel that any of this is inappropriate. When people talk about age appropriate hairstyles, and age appropriate dressing, well, whose age? And who are you?"

Follow her here.