It's always interesting to find out where successful people got their start.
Paul Smith - Left school at 15, he says he has a balance between - okay at design, okay at business, and is maybe more of a Stylist.
Thom Browne - Like Paul Smith, Thom Browne got his start working on the business side of fashion, as a kid, was also more interested in sports, and found a niche in the market focusing specifically on well made men's suits.
Great article, quick read; http://www.businessoffashion.com/2013/12/thom-browne-says-stay-true-to-yourself.html
Kate Spade and Andy Spade - Kate started at Mademoiselle magazine and Andy worked in advertising. http://nymag.com/fashion/10/spring/63806/index2.html.
Ralph Lauren - According to the RL Wikipedia page he's worth about 6.5 billion dollars. RL started as a salesperson at Brooks Brothers and then found a niche in the tie business.
Steven Alan - Steven Alan started his design career in retail. His niche is the shirt, the reverse seam shirt. It's not easy to find a lot of information on SA, but I like this answer/question from fashionista.com
How did you move from being a retailer and curator to a designer?
When I started making clothes, I didn’t really have a design background. I would just buy a bunch of old shirts and bring them to the factory and say, “I like this collar, I like this cuff” and kind of piece together what I wanted that way. I would just end up with something. Hopefully I would be happy with it—of course, sometimes I wouldn’t be.
This short article from Interview is worth reading and I like this quote.
"When people think of skaters, they think of, like, the 12- or 13- or 14-year-old kid. But in New York, it was the 18-to-24-year-old hardcore kid who wasn’t wearing any skate stuff. They’d wear a hat or whatever, but they wouldn’t wear the clothing,because it would fit badly and was bad quality, and skaters want to look good and pick up girls. So we slowly started making our own stuff."