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The First Shoe I Skated In As a Pro is an ongoing series that focuses on the sneakers worn by skaters when they first became professional athletes. Sneaker Report got the awesome chance to catch up with former pro skater and Sports Stylist, Cindy Whitehead, to see what sneakers she chose to become the #1 ranked female skater in the US for pool riding and half pipe at the age of 17. Today, Cindy is highly regarded as the world's leading sports stylist, having styled almost every celebrated athlete you can think of, while still finding time to fit in a good ride. 

Join us for the first installment of this series to learn about Cindy's early shoe preferences, how some athletes choose their signature look, and the impact she had on Puma's relationship to skateboarding.

Interview by Calvy Click (@clickmasterflex)

What was your first shoe worn as a pro and how did you choose it?
In the beginning, it was really strange because a lot of people wore Vans, I wore Vans casually, but to skate pools and half pipes I always wore Nike. Nike wasn’t as big as it is now, it wasn't an off-brand, but everyone wore Vans so I was kind of the odd man out in a way.

I always wore a white Vans with a swish in another color, whether it be navy blue or red. In the beginning when I was doing freestyle, I wore low top Nikes and then started to wear high top Nikes, so pretty much all of the pictures you see of me I’m in high top Nikes.

Shoes at that time were getting really expensive for my single parent and I was blowing through them right and left and I had skateboard sponsors, sponsors so I could skate free at skate parks, food, all of that stuff, and everything else, but not shoes. Shoes were – I don’t know—probably like $30, $40 a pop and back then that was a lot of money, so I basically found where Puma was located (in the OC back then) and made an appointment to meet with one of the CEOs and showed him my skateboarding "portfolio" of pictures and contest results and ended up getting myself a shoe sponsor. I told them that their shoes were kind of what I was already skating on, I liked the fit and the feel and thought it would be good as they were located in the OC. All the while my grandparents who drove me there waited in the car. It was kind of that easy. No one had approached them about a sponsorship and no one was riding for them yet, so Puma didn’t realize the correlation between their brand and skateboarding. I was 16, probably, and I went down there and just started wearing Pumas from them from then on out because they were free and they would send me boxes of shoes every month.

"No one had approached them about a sponsorship and no one was riding for them yet, so Puma didn’t realize the correlation between their brand and skateboarding."

I was always addicted to white sneakers and I don’t know why, but I’ve always been addicted to white. White high tops with the cream colored Puma stripe on the side or sometimes I would color the stripe in with markers or I would just leave it because it went with everything, so that was pretty much where I ended up with wearing the Pumas.

I like that you stuck with one color thought your career, not a lot of that going on now with all of the crazy colorways and prints offered today.
What I’ve realized from styling athletes is that it’s whatever you grew up with. I had an Olympic ice skater that I styled for 12 years or so and she would wear white ice skates but she hated white tennis shoes, she would only wear black sneakers. I asked her why once because it looked so chunky and heavy on her feet and she was so petite. She said that she had to wear white ice skates every day of her life and still did, so the last thing she wanted to do off of the ice was put on white shoes. So I asked some pro guys I work with that are not in the skate world, like why do you guys wear black shoes? And they would say "I grew up wearing black shoes, never had white shoes."

So everyone has their preferences, whether it’s dark or white or a color, now I’m a little bit more versatile, but I still tend to go for a white or grey shoe over a black one. Today I wear a lot of Converse and Vans. When I skated down the 405 freeway in LA, I wore bright hot pink Vans, which is unusual for me because I don’t ususally wear bright colors, but I had just gotten those and I hadn’t worn them in yet so I was like, oh these might be good, so popped those out and wore them. But Vans has always been my favorite for my casual stuff, and I don’t know I just never really skated in them in pools and I think I never did that because everyone else was.

What do you think of the skate shoes today that are built with from a performance standpoint?
I think a lot of the newer shoes are really great. For the pros that are out there today, those shoes are awesome. When we first started skateboarding, before people wore Vans they wore Converse and there wasn't a lot of support in those shoes, just in how flat they were and in the heel cup. Now you have skate shoes that have so much more support in the shoe, the way they lace up and fit tighter across your foot, altogether more supportive shoes. I think all of those brands are doing a much better job of thinking about what works for the sport, and that's a great thing.

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