Posted on January 26th, by HeatherZeller in BLOG, INTERVIEWS.


Cindy Whitehead merged her athletic experience as a pro-skateboarder with her fashion experience as a wardrobe stylist to become a “Sports Stylist®.” Whitehead developed this unique niche and coined the term herself.  She travels the globe to style some of the biggest names in sports like Kobe Bryant, Drew Brees, Tiger Woods, Mia Hamm and Michelle Kwan. Besides dressing athletes for personal appearances, Whitehead specializes in styling sports stars and models for athletic based ad campaigns, commercials and editorial spreads.

“I found there was a desperate need for sports styling and no one was doing it,” Cindy has said. “A lot of agencies as well as clients had no idea of trends for different sports and geographical areas. I wanted to change that.”

Sports advertising is big business, and major players like Nike, adidas, K-Swiss and Gatorade use Cindy’s services to effectively and accurately communicate their brand messages in the ads and TV commercials consumers often see. Whitehead ensures the fashions used are correct technically and on-trend for each sport.

A Glam Slam spoke with Cindy about being a Sports Stylist® and what it’s like to work with some of the world’s greatest athletes. Check it out:

(photo credit: Ian Logan)

You’re a pro-skateboarder turned stylist, a career change that is not too common. How did you transition into the world of fashion?

I always had my own style growing up. In elementary school I wore cowboy boots non-stop & rode horses every chance I got, which was not too common here at the beach. At age nine, my mom took my brother and I down to Mexico and Guatemala in a Volkswagen Van and we lived in it while traveling for a year. During that time my style was very hippie chick.

When I started skateboarding in my early teens I wanted to make sure I stood out from the predominately male group of skaters, so I had my sponsors custom make t-shirts for me in pink, yellow or light blue with my name in a contrasting color. I paired these with a variety of OP cord shorts that my grandmother would take me to buy, so that eventually I had every colorway they made. I also chose to wear Nike and Pumas to skate in and not too many girls were wearing those brands.

I realized that my fashion cravings were getting expensive for my mom, who was on a teachers salary, so I started approaching companies I liked and having my grandparents drive me there at age fifteen to have “meetings” and show my skating portfolio to talk them into giving me free apparel & shoes. I put together a letter about “why” they should do this, and what they would get from it,  i.e. photos of me wearing their product in magazines, etc. It seemed to work, and companies like Puma started supplying me with as many shoes as I wanted, anytime I wanted.

When I was about seventeen, I was up for The Skateboarder Magazine Awards and I did the same thing again. I approached an apparel company and asked for a dress to wear and explained what the event was and once again gave them photos/articles about who I was. They said yes, and sent a box of dresses over for me to choose from.

When skateboarding started dying down in the 1980’s I thought I wanted to go into TV or film production as a producer. I had been featured on some TV shows and watched what everyone did behind the scenes and thought that was the direction for me.

It wasn’t until a few years later that I found out there was such a thing as styling and headed in that direction with my career. It really makes sense now that I look back at how I dressed myself when I was skating and how I went about getting apparel. I do exactly the same thing now, but for other athletes, both male & female.

Describe the role of a “Sports Stylist®?” Is this a term you coined yourself?

I started like most stylists, doing editorial & celebrity shoots and worked my way up to style advertising shoots for clients like Coca Cola and Chevrolet. A few years into my career I met a photographer who was only shooting sports (at the time there really were not many photographers specializing in just sports). I started working with him a lot, and when more photographers came on the sports scene I decided to make the switch from regular styling to just working on sports related shoots. My agent at the time, warned me against this and told me I’d never get enough work in this niche market… And since I don’t like being told, “you can’t” when I strongly believe in something, we parted ways.

A few years later I coined and trademarked the term Sports Stylist®.

I am called in to style photo shoots and TV commercials that involve athletes excelling at their sport. My job is to make sure that everything is technically correct and current for the sport we are shooting and that the athlete, as well as the client, is happy with the direction of apparel. I also specialize in dressing athletes in more fashion type apparel for any events, TV interviews or magazine spreads they may have.

Does your experience as a pro-skateboarder help with this business?

Absolutely. I understand a bit of what the athlete is going through at these shoots. They are used to training & competing and sometimes a photo shoot is a whole new situation for them. It’s all about making them comfortable and them knowing you are not going to put them in something that is so far from who they are, that they feel ridiculous.

When you first began as a Sports Stylist®, was it difficult to convince companies that they needed your services?

Most of the companies, like Gatorade and Nike, got it immediately and were stoked to have someone who understood what they wanted/needed. They also appreciated that I was not going to try and make it into a “fashion” shoot, if that was not what it was about. But even now there are some clients who don’t fully realize all that I do, or what I can offer them, until they work with me. But I like that, a challenge is always good.

Major brands like Nike and adidas now use your services to help communicate their brand messages in an authentic way. How do you ensure that this is done?

By constantly researching the sport, the athletes and reading/watching everything I can about the sport we are shooting. I also gently communicate with the client when something they want “crosses the line” of authenticity and see what we can do to keep their vision in line with what is “real” in the sports world. A lot of sports are setting/making the trends so that is another things you want to be able to show realistically.

Staying up-to-date on trends across all sports seems to be an important part of the job. Is that a difficult task?

It is, because I deal with a vast array of sports that range from horse racing to ice skating to surfing and BMX.  I also have all types of team sports, ranging from mainstream sports like football, & baseball, to lesser known team sports (at least in the USA) like lacrosse and rugby.

Athletes have very different physiques than the rest of us. Does this pose challenges when styling?

Athletes have unique bodies. When you dress models and actors, they tend to be (for the most part) clients who can usually wear sample sizes. I have athletes that range from 4’10 to 7’6 so sample size isn’t always going to work.  It’s my job to know how to emphasize their bodies and find things that make them look and feel good on and off the field/court/etc.

Some athletes must be hesitant to take fashion risks when need be. What do you do to get them on board?

By gently asking them to be open, “just try it on”, and reminding them that “trying it on” doesn’t mean you have to wear it. Sometimes that is all it takes to encourage someone to step out of their comfort zone. We all have a “vision” of what we look like and we tend to stick with what we “think” looks good on us. Sometimes it takes someone else to view you in a different light and encourage you to try new things.

I had an Olympic athlete who always wore black to all her events, as I gained her trust we started trying pops of rich color on her for some fashion spreads she was featured in. She ended up loving it, and while she doesn’t chose to deviate from sold black on her own, she will venture in another direction when I come in to do her appearances and shoots.

You really need to gain the athletes trust, and know not to ever bullshit when something doesn’t look good, as they will never trust you again.

You’ve worked with a lot of pro and Olympic sports stars. Who would you rank among the best-dressed?

It’s hard to pin point just a couple. In general I would say that the NBA has a lot of guys with amazing style off the court. They tend to take more fashion risks than most. And because I always love a casual boho vibe, I’d have to say that the women in action sports rule that look on all levels.

Are there any specific shoot(s) that stand out as your favorite?

I think the first time I was hired to style Pro Surfer & shark attack survivor, Bethany Hamilton was pretty special. Not only is she an amazing athlete, she is an inspiration to many, many people, including myself. I knew about her story and followed her journey for years, so being asked to work with her each time is always a pleasure. She is so sweet and fun. I really love her.

And as for you, how would you describe your personal style?

Boho Chic meets Skater Girl meets the Girl With the Dragon Tattoo.

Check out some samples of Cindy’s work below and you can view more here:

(photo credit: Tim Mantoani)

(photo credit: Steve Bonini)

(photo credit: Patrik Giardino)

(photo credit: Marcus Paulson)

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  1. Awesome interview Cindy!

    You are the “GO TO” gal for anything sports, and beyond. There are alot of details to keep track of and you have your finger on the pulse!

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