Cindy Whitehead – Sports Stylist®

The Active Team had a chance to talk shop with former pro skateboarder-turned-Sports Stylist®, Cindy Whitehead in LA last month…and we are pretty sure that we may have met our long lost creative soulmate. We have had a “girl crush” on Cindy for a little longer than we would like to admit — as it is very rare to find other women that LOVE fashion and sports as much as we do. We have been reading her blog, following her on Twitter and keeping tabs on her evolving Pinterest, so when we finally decided to reach out, it felt more like we were asking for her phone number than an interview.

Photo by Shawna Reyes

Cindy was one of the first professional female vert skateboarders in the U.S., and is regarded as a pioneer in women’s action sports. At the ripe age of 17, she was ranked the #1 female skater in the country for pool riding and half pipe, and to this day she still holds the title for being the only woman to be featured in the centerfold for the iconic Wild World of Skateboarding.

Photo by Bruce Hazelton, Wild World of Skateboarding

In the late 70s, Southern California gave birth to a movement that would unknowingly shape contemporary sports culture and the modern definition of “All-American pastime” forever. As teenagers began to put down baseball bats and pick up surf and skateboards, the status quo shifted, shining a light on an alternative crop of young trendsetters. The local crew associated with this scene, including Cindy Whitehead, would pave the path for generations of future rippers, looking to emulate not only that specific SoCal style of skating, but also the aesthetic that went hand in hand with that lifestyle. When Cindy retired from skateboarding at 22, she yearned to combine her passion for sport with her creative sensibilities, uncovering a niche category that would eventually set the tone for her future career as a Sports Stylist® – a term she actually coined years later.

Photo by Steve DePinto, Vision Street Wear

Today Cindy is regarded as the “worlds leading Sports Stylist®” boasting an impressive roster of clients from all walks of the active community. From athletes like Tiger Woods, Kobe Bryant, Drew Brees, Mia Hamm and Peyton Manning to brands including NBA, Nike, Adidas, Levi’s, Gatorade and Coca-Cola, Cindy has helped mold the look and direction, once again, of contemporary sports culture.

Gatorade – Steve Bonini, Paul Rodriguez – Bo Bridges,  Lucy – Larry Bartholomew, EA Sports – Tim Mantoani, Nux – Ian Logan, Michael Phelps – Tim Tadder, Burton – Ron Eshe

Make sure to check out the full profile on Cindy in the Active section and visit her site Cindywhitehead.com! –Jeanine Pesce




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