(Pretty) Radical, Smart and Bitchin’

By the time she was inducted into the Skateboarding Hall of Fame by rocker Joan Jett in 2016, local legend Cindy Whitehead had ridden many, many miles. Cindy is on a mission to empower the next generation of female skaters to share their stories with the world.


This anthem by Joan Jett, her musical heroine, is one of Cindy Whitehead’s all-time favorites. And if you talk to Cindy for more than five minutes, you’ll understand why. A spirit of fun, challenging societal norms and living life on her own terms has defined her most of her life.

She is quick to acknowledge, however, that back in the 1970s when she was growing up, most folks living in the South Bay were very accepting of her as a female skateboarder. “If it wasn’t for the people in the South Bay,” she says, “I probably could not have accomplished all that I have.”

Her grandmother was her first champion and gifted her with a skateboard for her 14th birthday. As the owner of the Tu’u boutique on Pier Avenue and an active community member, her grandmother embodied female empowerment.

Her message to Cindy was always: “Mark your own path; do what you want to do. Don’t just follow what everyone else is doing.”

The skateboard that Cindy’s grandmother gifted her had Cadillac urethane wheels, purchased at ET Surfboards in Hermosa Beach. Cindy loved the freedom that skateboarding afforded her. Many of Cindy’s friends and fellow skateboarders were guys, but her best friend was Michelle Kolar—another local girl who would become a national freestyling champion.

Every now and then Cindy and Michelle would encounter other female skateboarders on The Strand or at the local skate parks. “You’d see a few doing freestyle and snake runs,” she remembers. “Vert became popular with the emergence of half pipes and pools.”

The first wave of female skaters from the ‘60s and early ‘70s were falling out of the sport because of injuries or because they were getting older and moving on to other pursuits. Cindy and Michelle were at the vanguard of a new generation.

Also at this time Cindy was attending Mira Costa High School in Manhattan Beach, and she would often ditch her classes to participate in demos. With the support of her family, the school eventually agreed to let her attend half-days in the hopes that this schedule would keep her in school and on track to graduate. She took only core subjects like English and math in the morning and received elective credits to practice skateboarding in the afternoons.

Her skateboarding passion would once again pose a significant conflict of interest, however, when she was invited to participate in her first skate tour. The event required that she travel for three weeks. Compounding the challenge was the fact that, at that time, the school district had instated a new ruling that no student could be absent for more than 10 days per semester before getting kicked out.

The initial solution posed to Cindy and her family was placement in a transitional high school for challenged, on-the-verge-of-dropping-out kids. Both Cindy and her counselor said, “No way,” and her counselor successfully advocated for a tailored curriculum of correspondence courses that she could work into her schedule.

This plan worked really well for Cindy and (eventually) other skaters, who would do their homework on plane rides and whenever they had downtime. Thanks to this game plan, Cindy successfully completed her junior and senior years of high school.

Cindy’s first big skateboarding competition was the freestyle 1978 Hang Ten Skateboard Olympics at Magic Mountain in Valencia. As confident and trailblazing a person as she was (and is), the prospect stressed her out big-time.

She had a vision for how she wanted her routine to unfold, but since her management wasn’t attending to what she saw as very important details, like music, she decided to handle them herself.

She also decided that she did not want her friends or family to attend because she believed that their presence at the event would stress her out even more.

Thankfully they defied her wishes and took a ton of pictures that ended up being the only documentation of this seminal moment in her skateboarding career. Skaters from all over the country participated in that competition, and among the women Cindy came in third place.

She participated in many other competitions after the Hang Ten Olympics and became one of the top-ranked professional female vert skateboarders in the U.S. for pool riding and half-pipe. She was also the first professional female skateboarder to be sponsored by Puma and skated professionally until 1982.

Right around this time, skate parks across the country started closing down because parents would sue them whenever their kids got hurt. Cindy decided to “get a job, figure out ‘real life’ and move on.”

After attending UCLA briefly, she found work as a production assistant on several movies and also worked in Mattel’s photo studio. She eventually took a job as a stylist at a magazine called Swimwear Illustrated, which was based in the Bay Area. The magazine was launched by the creator of Runner’s World and served as a great training ground for what would eventually become Cindy’s professional niche.

After working there for only one year, Cindy moved back to the South Bay and landed an agent in Los Angeles who connected her to styling gigs across the area. Cindy began working on print commercials, catalogs and editorial spreads for companies such as Toyota and Volkswagen.

Sports were still Cindy’s passion, however. After a few years her photographer boyfriend (who would eventually become her husband) helped her reexamine her focus. With his support, she came to the realization that she wanted to focus her expertise on sports—even though she was working with some of the biggest companies, actors and musicians in the world.

Her agency dropped her when she told them her decision, and Cindy became a free agent—finding gigs on her own. She coined and trademarked the term Sports Stylist® and has worked with some of the top sports photographers in the world for clients like Nike, Adidas and TaylorMade Golf.

But a love for skateboarding never left Cindy, and even though she stopped competing, she never stopped skating. In 2012 she embarked on a renegade adventure that propelled her back into the public eye. Remember “Carmageddon II,” that dreaded final weekend in September 2012 when portions of the 405 Freeway were closed for construction? The royal inconvenience that had most of Los Angeles planning their Netflix queues for the weekend got Cindy and her husband, Ian Logan, strategizing how she could skate down an empty 405 Freeway.

On the morning of Sunday, September 30, police were stationed at every on- and off-ramp of the 405. As they drove around the Sepulveda Pass near Getty Center Drive, Cindy and Ian got pretty discouraged. They were about to turn around and head home when they saw it: a hole in a fence and no police cars in sight.

Cindy recalls that her husband told her to run up onto the freeway and just start skating. She did, and he caught the whole thing on film. They jumped back into their car after only a few minutes because there was a police car stationed at the next exit.

After they got home, they downloaded the images and put one on Instagram. Their use of the hashtag #carmageddon resulted in their post being seen by The Huffington Post, which broke the story shortly after. Soon after, other big media outlets like CBS, ABC, NBC and ESPN were broadcasting the story as well.

One day Cindy and Ian found themselves talking to the creative director at skateboarding company Dusters California. The creative director posed to Cindy the idea of designing a skateboard with Dusters’ parent company, Dwindle—one of the world’s largest skateboard manufacturers. Cindy said yes, excited by the prospect of designing a board for girls since there were so few on the market. She even created the artwork.

Shortly after it launched, 200 of those boards sold out on the Vans Warped Tour in less than 20 days. The board began getting a ton of press, with stores clamoring to carry it. And because Dwindle’s distribution is worldwide, Cindy’s board started showing up as far away as China and Japan, where girls carried it like a purse.

“People should embrace individuality-in themselves and in others. I hope that we’ll all encourage future generations to go further than we’ve gone; that’s the key. We need to be the women that embrace other women-not think that they are the competition. Collectively, together, we are so much stronger.”

A skateboard shop in the Middle East picked it up too and sent Cindy a picture of a local girl holding it. Startlingly, the girl in the picture wasn’t covered in a hijab but simply standing in the shop—no differently than a Western girl would. Cindy was blown away by the implications of the image, as it exemplified how in places where females are limited by social mores and punitive laws, skateboarding is serving as a vehicle for rebellion and social change.

As it turns out, a growing number of girls and women skate in places like Tehran, Iran, but usually under the protective veil of night. Some of these brave souls even send Cindy pictures—but with a request that she not post them on social media. If they can, some girls even fashion their appearance to look more like boys, just so they can get away with skateboarding in broad daylight.

“It’s really cool,” Cindy says, “but obviously it shouldn’t be this way.”

To date Cindy has seven boards in the Dusters California X Girl is NOT a 4 Letter Word collaboration. Each one features the logo of a nonprofit they select for that edition, and it’s always a female-based nonprofit that supports female skateboarders.

So far, those charitable recipients are the Poseidon Foundation (which encourages female skateboarders across the globe), GRO (Girls Riders Organization), Exposure Skate (which organizes the largest all-female contest annually) and Bridge to Skate (a nonprofit that supports female skateboarders in the inner city). Dwindle matches her dollar-for-dollar on every donation, and a check is sent directly to the nonprofit each quarter.

Cindy launched the company Girl Is NOT a 4 Letter Word in 2013. The brand sells merchandise aimed at female skaters and features interviews and news about females in action sports on the website. Cindy’s next project will be micro-grants of up to $250 for girls who want to create their own media—be it a social media campaign or a ‘zine.

Even today, Cindy says, the skateboarding industry is still creating very little media with female content. As in, magazines will go months and months without putting a single female in their pages. When asked why she thinks that is, her answer is simple: Because it is still a male-dominated sport.

So the micro-grants are intended to provide an antidote. She states, “I’ve had girls come to me and say, ‘Hey, we want to jump in a van, and we want to go from Colorado to California and skate everywhere we can. We’re going to do a Kickstarter campaign.’ And I’m like, okay, so why should they have to do a Kickstarter? It takes a lot of effort, and with so many Kickstarters out there, people are immune. Why not give these girls the opportunity to apply for a micro-grant?”

Cindy’s company also recently released the first hardback comprehensive female skateboard book ever published. Entitled It’s Not About Pretty: A Book About Radical Skater Girls, the book has been well-received and was written up in such outlets as Forbes, Teen Vogue, Marie Claire and Skateboard.
It is sold in retail outlets around the world. Cindy couldn’t be happier about this, because the book has afforded her yet another way to ensure that the awe-inspiring journeys of female skaters are shared with others.

The book features images of 65 female skaters, ages 5 to 50+, which Ian has shot over the last five years. A 24-year-old female skater in Florida, Elise Crigar, handled the design. Ian’s condition for contributing to the book was that he wanted to put up all the money and create a high-quality coffee table book that girls could be proud to display in their homes—complete with Smyth sewn binding, top-notch paper and saturated images.
Cindy says, “He told me, ‘You figure out how to make it awesome, and I’ll work out the cost.’” The book paid for itself in the first two months.

Moreover, it can be found in seven public libraries throughout Los Angeles County. Most of these libraries could not afford the book, so Girl Is NOT a 4 Letter Word donated them. In order to earn a place on the shelves of public libraries, they had to register the book with the Library of Congress, which was somewhat labor-intensive but necessary in order to make it accessible to a larger audience.

Currently each copy is sold sealed, with a sticker that says: “1 of 4 Posters Inside.” The posters are 15” x 19” and are intended to serve as inspiration for girls who might even want to put them on their wall.

Cindy shares that when she was growing up, she would cut the often very small pictures of female skaters out of magazines and use them to create inspirational collages. And when she herself eventually made the centerfold of a skateboarding magazine, she cared less about being the person on someone’s bedroom wall and more about being the person that some girl out in the world could be inspired by—even if her parents sometimes discouraged her from skating or people she knew were making fun of her for it.

The title It’s Not About Pretty actually first appeared on one of Cindy’s boards—an ironically bright pink number in which the phrase was spelled out in gold punk-style lettering. The idea behind the phrase, says Cindy, is that being a female skater is about being “pretty radical, pretty smart, pretty bitchin’.” She acknowledges that it’s fine for a person to want to look their best for themselves, but she wants girls to understand that there’s more to life than just looking good.

Cases in point: In the book you will find an image of an incidentally cute girl who proudly shows the gash she acquired after crashing down a hill at 30 miles per hour. And then there’s the girl with a goose egg bruise on her head and a smile that conveys the unabashed joy she takes in the sport. Cindy notes that when the girl discovered her photo in the book, she was thrilled about that bump because she thought it made her look “bad-ass.”
When she was nominated for inclusion in the Skateboarding Hall of Fame, Cindy was tasked with selecting the individual who would introduce her. And so she boldly emailed Joan Jett, even though they’d never met, explaining to her how much her music meant to her back in the day.

Joan responded to her email within 12 hours. Cindy and Joan are now friends, and Cindy appreciates the emotional support that they provide to one another. Joan’s advice to Cindy has included this bit of wisdom: It doesn’t get any easier challenging the status quo, but when people tell you to be quiet, just talk louder.
“We all need support,” Cindy says. “As women, we’re all helping the next generation, and it makes us collectively stronger. It’s a good thing. The fight for equality is not just a female fight. We have males helping us too. Ian has been instrumental. A guy names Ted Coombs who set up my first skate tour for me was instrumental.”

And now Cindy believes it’s her job to help others. She has signed nine pieces of her skateboard history over to The Smithsonian’s National Museum of American History sports collections, and another seven are on loan to the Hermosa Beach Historical Society museum. She’s also given a TEDx Talk. But there’s still so much work to be done.

When asked for a final thought on her skating career and current mission, she shares this: “People should embrace individuality—in themselves and in others. I hope that we’ll all encourage future generations to go further than we’ve gone; that’s the key. We need to be the women that embrace other women—not think that they are the competition. Collectively, together, we are so much stronger.”


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