Jenna Lyons, former Creative Director and President of J. Crew until 2017, as well as all-around style icon, was known as "the woman who dresses America" (NYTimes). She has spoken openly about her awkwardness growing up, exacerbated by her genetic condition, which affected the normal growth of her hair and teeth, and still wears dentures.
I think there's a common misconception about designers, and clothing designers in particular -- that they became designers because they love beautiful things. I've worked as a clothing designer for almost 10 years, and in my experience, people become designers because -- like Jenna Lyons -- they have had significant, formative events that taught them the real power of clothes. And they want to take the power and share it. Design studios are filled not with obsessive fashionistas or shopaholics, but artsy, introspective creatives who value self-expression over commodity. Individualism and experimentation reign, and the biggest style faux-pas is imitating someone else.