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29. American Apparel
American Apparel is a twenty-something geared apparel brand that is known for its risque ads and for casting barely-legal models. Which was why it was such a pleasant surprise when they cast Jacky O'Shaughnessy, who was 62 at the time. 

"I was game the whole time," O'Shaughnessy told Elle. "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?"