Today we’d like to introduce you to Cindy Whitehead.
Alright, so thank you so much for sharing your story and insight with our readers. For folks who have missed our prior interviews with you, can you start by sharing a bit about how you got started?
I was a pro skateboarder in the late 70s, and when I was interviewed on TV or by a magazine, I’d ask what each person did and little questions about their job, like how they got there and what their day was like. It gave me a glimpse inside of another world firsthand, and I soaked it all up. I found the whole behind-the-scenes part of these shoots so interesting. I also knew that the reality was that I wouldn’t be a competitive skateboarder at the pro level forever, and I wanted to start figuring out what was next. Even though I was seventeen, I knew that for me, it had to be something I was excited to do each day and as challenging as learning tricks in a half-pipe or pool on my skateboard. That’s a tall order! After skateparks started closing and competitions and money coming in was scarce, I started making a plan. First, I attended UCLA, took film and television courses, and learned about production and screenwriting. Next, I looked into becoming a stuntwoman as I was athletic, had great balance and timing, was small, and looked younger than my years – so I could double for children, which was a good niche. I also took a few acting classes at The Lee Strasberg Insitute and realized that was not the side of the camera I wanted to be on. So, I dropped out of classes at UCLA and started doing PA work on films – the hours were long, and I wasn’t fond of the lengthy schedule and weird hours it takes to shoot a movie. Next, I looked into the photography industry and worked in the photo department of Mattel Toys for just over a year. That world was so me – I could tell it was a perfect fit. But I wanted to be out of the corporate environment and studio and work somewhere more interesting. So, I contacted a magazine, SWIMWEAR ILLUSTRATED and asked for an interview. They were based in San Jose, CA, so I flew up in the AM, met with the CEO, and by 2 PM had a solid job offer to do production for their photo shoots. The best part was I scored the interview because on my resume, under special interests, it said that I was a pro skateboarder. The CEO said he didn’t have a position but wanted to meet a pro-female skateboarder and hear what that was all about. But after speaking with me for over 2 hours, he decided to create a position for me and let me run with it.
During the year I was there, I set up shoots for the magazine, models, and crew in Mexico, Jamaica, Greece, Spain, Morocco, and some USA travel destinations. I traded ad space in the magazine for hotel and air we needed and learned as I went. Later on, I bluntly asked if I could style the shoots as well. The magazine was filled with models in swimwear in amazing locations, but I felt like it needed more – a prop here, an accessory there. So that’s how I got started in styling. When I left the magazine, I went back to Los Angeles and got a styling agent – I went on to style young celebrities and do mainstream ads such as Toyota, Bank of America, and the like. But again, after a few years, I felt like this was not what I wanted to be doing, so I asked my agency if I could start specializing in athletes and sports – as Nike and Adidas were now running big ads and sports were beginning to become a “thing.” They laughed and said they’d cut me from the roster if I didn’t do the other mainstream work as well. I took a leap of faith, went out on my own, and worked directly with the two most prominent advertising sports photographers during that time on every single project they had. I have broadened my roster to include some of the biggest names in photography and a client list filled with top-notch sports companies and pro and Olympic athletes. At this point, I started calling myself a Sports Stylist® and trademarked the name. I eventually signed with an agency in NYC (even though I am based in LA – I work all over the world), and they are wonderful. They get me, get what I do, and always encourage me to expand and change to suit my needs. Every shoot day is different, and I have athletes I have worked with for over 15 years – some I met and worked with when their careers first started. So it’s nice to have that familiarity in knowing their likes/dislikes and watching their careers expand over the years we have worked together. I get hired because of my vast portfolio, along with my knowledge of just about any sport, my sunny California personality mixed with a “yes, I can absolutely make that happen” NY-style attitude, and sometimes even the fact that I was a
pro athlete myself and clients know that I get it. Of course, the fact that I know and love fashion doesn’t hurt either.
Would you say it’s been a smooth road, and if not, what are some of the biggest challenges you’ve faced along the way?
Some of the more complex lessons have been how to gently explain to a client or room full of advertising agency executives that what they have envisioned apparel or prop-wise may not be authentic for that particular sport and how we can work to incorporate their ideas while remaining true to the athlete. At the beginning of my sports styling career, I only had male athletes and started to quickly realize that was because men in sports were paid large amounts to endorse products. Female athletes were not thought of that way, as clients had not yet learned that they could sell products just as well as their male counterparts. That always bothered me. Luckily things have started changing, and I get to work with some fantastic and powerful female pro athletes. I am now asked to speak up about which female athletes might be good for a campaign, and I love that I get to sing their praises. I also find it hard to watch some of my athletes compete at the Olympic level – if they don’t perform as well as they wanted to, it affects me, as I am emotionally invested from being so close to them throughout the years.
Can you tell our readers more about what you do and what you think sets you apart from others?
I specialize in wardrobe styling for ads, commercials, and editorial shoots, working with everyday athletes/models to well-known pro and Olympic athletes. I trademarked the name Sports Stylist® back when I created this niche for
myself, and I am known as the “go-to person” for my specialty. I know a lot about most sports, as I work in them often, and sports that I don’t know about, I research thoroughly beforehand. The same goes for athletes. I can tell you that a pro ice skater only has one pair of skates that are broken in (and it takes a long time, and they hate the process), so don’t ask them to bring a “back-up.” I know that a rock climber sizes down in rock climbing shoes from
their regular shoe size. You need to know in baseball and golf if someone is right or left-handed, as that makes a difference in the equipment you pull. Cowboys always want their Stetson hats put down on the crown, so the brim stays flat. I could go on and on… I am most proud of the fact that athletes and agents ask for me by name to be on whatever project they are working on because they know I will be an asset to the athlete while also making sure the agency/client is 100% happy with everything as well.
Can you talk to us a bit about happiness and what makes you happy?
At the end of the day, a successful shoot makes me really happy – when I see the client, agent, athlete, and crew smiling and everything went smoothly, that to me is the best! I also enjoy seeing the finished project come out, checking every detail, and seeing that we killed it!
Contact Info:
- Website: www.cindywhitehead.com
- Instagram: https://www.instagram.com/sportsstylist/
- Facebook: https://www.facebook.com/SportsStylist
- Twitter: https://twitter.com/SportsStylist
Image Credits
Ian Logan Elise Crigar Aaron Lieber Trevor Pearson Craig Cameron Olsen Tim Mantoani Attiba Jefferson
