Alexander Wang
Alexander Wang

My mom would put me in these preppy little suits and slick my hair to the side. I have these baby pictures of me where I'm this little preppy kid with a sweater tied around my neck.

Brad Goreski
Brad Goreski

I am preppy, geek-chic with a touch of Bozo the Clown with a touch of 'Showgirls.' Sometimes, I look at myself and think I should put on a red nose, white face and maybe entertain some kids.

Cassadee Pope
Cassadee Pope

I came from a private school, and public high school was the first time I ever went to a public school. So I went into it very preppy; I was wearing a lot of Abercrombie and Hollister. Then, my sophomore year, I started listening to rock bands. I had a boyfriend that took me to my first rock show, and I was just addicted to that.

Christian Siriano
Christian Siriano

Well I am from Annapolis Maryland. I went to High school in Baltimore, but I grew up in Annapolis. It was a cute town. We lived on a waterfront community. It was good, even though I don't really fit the preppy boater kind of style.

Emily Weiss
Emily Weiss

I grew up in a conservative New England town and showed up to my middle school orientation dressed like 'Clueless' while everyone else was wearing J. Crew and lacrosse uniforms. I never really fit into that preppy look.

Hannah Kearney
Hannah Kearney

In my personal life, I really like the look of vests. I wear fitted, business ones, and perfectly preppy sweater vests that I can knit myself.

John Waters
John Waters

I went through different looks. At one period, I was preppy because that's how I grew up. But then I had bleached hair in the front. And I used to wear - then I wanted to be a beatnik. It was hard to be a beatnik in suburban Baltimore. But I wanted to be one.

Kate Spade
Kate Spade

I was preppy, then suddenly switched around age 14. I asked my mother to go to this vintage store, and she let me buy a leopard swing coat, pink cigarette pants, and lime-green gloves.

Kellan Lutz
Kellan Lutz

I am very picky with my career. I don't need to do it for the money or the fame. I'm very choosy, which is why I haven't played the typical role that people expect to see from someone of my stature and size, as the mean jock or the preppy. It's very easy to see me like that. That's why I go against it in different roles.

Loudon Wainwright III
Loudon Wainwright III

When you start your career, you have to figure out a way to separate yourself from the pack. So I went for a kind of preppy, psycho-killer look: I had short hair, grey flannel pants, and a button-down shirt. I think it worked, because nobody else was looking that way at that time.