Interview: Professional Skateboarder Turned Celebrity Sports Stylist, Cindy Whitehead

At the age of 17 and with only two years of skateboarding under her belt, Cindy Whitehead was ranked the number 1 female skater in the United States in pool riding and half pipe. After much success in her field, “including the distinction of being the only female skater to be featured as a centerfold in a top skateboarding magazine,” Whitehead retired from the sport she knew and loved at the age of 22 and began a career in styling. Never one to let fear or obstacles stand in her way, Cindy saw a need for sports styling on sets and decided to make the career of her dreams her own. (

CWHllywdBlvdProfessional Skateboarder turned Sports Stylist, Cindy Whitehead – Photo credit – Ian Logan


How She Went From Pro Skateboarder To Stylist

Candie Anderson: As an accomplished professional skateboarder, did you have any aspirations to work in fashion?

Cindy Whitehead: “I always loved fashion but was more into surf/street style when I skated. I was sponsored by various companies and most were nice enough to humor me and make custom made tee’s for me in the color ways I requested and the girls versions of tees. It’s a male dominated industry, so back then girls just usually wore what the boys wore. I also tried to make sure my ‘look’ stood out when skating with all boys. When there were award shows for us skaters, I would call women’s surf wear companies, run my pitch by them and see if they would send some cute things over for me to wear in exchange for promotion. So even then I had some thoughts on fashion and what worked/looked good and was different. I was happy to set a trend rather than just simply follow it.”


CindySkateboard candace rose interviwAt age 17, “Cindy Whitehead was ranked the #1 female skater in the US for pool riding and half pipe.”  –; Photo credit – Brad Bowman

CWCenterfold“To this day Whitehead holds the distinction of being the only female to be featured in the centerfold for a top skateboarding magazine.” –

What Inspired Her To Become A Sports Stylist

Candie Anderson: What led you to a career in sports styling?

Cindy Whitehead: “I worked at a swimwear magazine based near San Francisco, California, as a stylist and traveled all over the world shooting girls in swimwear and adding accessories and pieces of actual clothing reflecting where we were (Morocco, Greece, Spain, Mexico). After a year of working there, I then came back to Los Angeles, got an agent and started doing more of that plus working with younger celebrities.

One day I met a photographer who was ONLY shooting sports/athletes for magazines and some advertising, and we started working together (my background of being a pro skater helped open doors and trust with athletes and their management team.) About a year or two later, the world of advertising started exploding – showing athletes in everything from Nike shoes to car ads. I decided early on to stop doing other types of styling and create a niche as a Sports Stylist® and focus on what I loved. My agent thought I was crazy, we parted ways and I went out on my own…”


A Typical Day Working On Set With Pro Athletes

Candie Anderson: What is it like working with some of the biggest names in sports?

Cindy Whitehead: “It’s awesome. Athletes are very respectful, they have grown up their whole lives listening to coaches and doing what’s asked of them each and every day, so being on set is no biggie for them. I never got comments that I would hear in the ‘celebrity world’ from female athletes, like ‘do I look fat?’ etc. These girls work HARD for this body they have and it’s meant to perform, they appreciate their body for what it does, even if it’s not a size 2. So wonderful. I am also fortunate to see things up close that the average person will never see when an athlete is performing.”


Onset katrina hodgson candace rose interviewKatrina Hodgson of “Tone it Up” being styled by the one and only Sports Stylist®, Cindy Whitehead for M&F Hers magazine. You can find Katrina & Karena of Tone it Up on Twitter – Photo courtesy of “Tone it Up.”



Yao&Cindy copySports Stylist®, Cindy Whitehead styling former NBA star, Yao Ming. Photo credit – Steve Bonini

Lucy1-1Cindy styled this ad for LUCY Activewear in both Los Angeles and San Francisco, California. Photo credit – Larry Bartholomew

Favorite Athletes That She Styles

Candie Anderson: Do you have any favorite athletes that you’ve styled?

Cindy Whitehead: “I styled ice skater, Michelle Kwan, for many, many years and we became very close; the USA soccer team has quite a few girls I have styled and at one point in time they all lived down the street for me, so that was fun. Pro surfer, Lisa Anderson, was my idol growing up, so that shoot was awesome in every way. Anytime I get to style action sports, (skateboarding, surfing, bmx, etc) I am stoked. Derek Jeter, Tiger Woods, Michael Phelps and Kobe Bryant are all fun to work with year after year. I can’t say that I have ever worked with a pro or Olympic athlete I did not like!”

A Few Pro Athletes That Cindy Whitehead Has Styled

Drew Brees EA Sports PS3Sports Stylist®, Cindy Whitehead styled Super Bowl champion quarterback, Drew Brees of the New Orleans Saints for the cover of Madden NFL 11. Photo credit – Tim Mantoani

Sergio Garcia PGA Tour Golfer in AdidasSpanish golfer, Sergio Garcia of the PGA Tour and European Tour in an ad for Adidas. Photo credit – Steve Bonini

  Michelle Kwan InStyleOlympic medalist figure skater, Michelle Kwan was styled for this spread in InStyle magazine. Photo credit – Kurt Markus

Nike Matt Holliday Jason Heyward Cindy Whitehead interview Candace RoseMLB players, Matt Holliday and Jason Heyward were recently styled by Cindy for this great Nike ad. Photo credit – Steve Bonini

Michael Phelps16-time Olympic medalist, Michael Phelps. Photo credit – Tim Tadder

And my personal favorite – FEAR THE BEARD!

Brian Wilson Cindy Whitehead Stylist Steve Bonini Photographer SF Giants Closer Pitcher Nike Ad Fear The Beard Candace Rose Anderson InterviewSan Francisco Giants closing pitcher, Brian Wilson. Photo credit – Steve Bonini

A Typical Day On Set

Candie Anderson: What is a typical day like on set?

Cindy Whitehead: “It starts prior to the shoot day with numerous conference calls, meetings, layouts that I need to look at; decipher and discuss with the photographer, art director, as well as clients. From there my team and I start planning what’s needed from our end. The client may be Federal Expressing us the main wardrobe, (or not) but we may need to spray paint balls; goggles; track shoes gold, like I did for an ESPN feature for the Olympics; or we may need to do a wardrobe pull from the ground up to create a whole series of looks as the ad is for cars or a sports drink. There is a lot that goes into the prep of these shoots.

For me being comfortable in what you are wearing is a must. There is a lot of running around, kneeling to fix things, and the weather can change from hot to cold super fast. 80% of the time my shoots are outside, not in a studio or other environment. Once we arrive on set (usually very early morning) my assistants start setting up the racks; loading in the wardrobe, laying out the shoes, props and accessories. From there we do a walk through with the photographer, client, ad agency and sometimes the athlete as well. I present what the vision is and we may all agree or make minor adjustments from there. Then it’s time for the hair and make-up team to start; then I start getting the athlete dressed and head out to start shooting. Breakfast and lunch is provided on set and usually there are plenty of healthy choices along with amazing brownies or something sweet for those who want them for dessert.”


Favorite Items and Brands On Shoots

Candie Anderson: I’ve mentioned many times how much I LOVE your style; what are your favorite brands/items on shoots?

Cindy Whitehead: “Thanks so much!! I keep it pretty simple in what I wear everyday on set. It’s usually some sort of broken in jean – either Current/Elliott, All Saints or j.Brand; a top by Rick Owens, Thomas Wylde, Calypso or Splendid; a lightweight sweater by James Perse, Velvet or The Row. Shoes are always some sort of flats by either Rocco, Sigerson Morrison, Calleen Cordero, or flip flops from Haviana (they feel like cushions on your feet when standing all day) or if it’s cold, boots by Golden Goose or Isabel Marant are my picks. I have this insanely rad down jacket by Rogan that goes on every road trip with me that I love. In the winter an Alexander Wang beanie is always in my bag and I am never without a backpack by either Lululemon or Burton – they hold my whole life!”


Cindy Whitehead’s Personal Style Essentials

Candie Anderson: And in your life?

Cindy Whitehead: “I wear similar brands that I would wear to work and the same layering type look, but usually in more delicate fabrics than I would wear on set. I will also do shoes with some height to them (5 inch heels being my max.) I have a Rick Owens jacket that I love to pair with everything from dresses to jeans and a tee. I also add a slouchy or interesting bag – right now my PS1 bag in this cool midnight blue is a favorite to carry. My accessories stay pretty much the same – a few rings, layered necklaces and some bracelets by Scosha that I never take off. I also have a silver Tom Binns bracelet on my wrist that looks like the Cartier Love bracelet, but when you look closer you can see that instead of their symbol of the circle with the line in it, Tom Binns (rad as he is) has made it into an “A” for Anarchy. LOL”


Cindy Whitehead JewelryCindy Whitehead’s gorgeous jewelry display


IMG00474-20110625-1721The ever-so-stylish Cindy Whitehead with the Tom Binns Anarchy bracelet I am currently coveting! Photo credit – Ian Logan

Paddedimage725600-TC46 - TOM BINNS DESIGN - TOUGH CHIC COLLECTIONTom Binns Anarchy Bracelet – Tom Binns

Items Cindy Is Coveting For Summer

Candie Anderson: Are you coveting any items for summer?

Cindy Whitehead: “It seems that I am almost always coveting or trying to track down some elusive piece. Just about everything from the Isabel Marant line is on my ‘want’ list (as usual) and still mulling over that chunky YSL Arty Oval ring in turquoise. I am very lucky to have such great stores near me like Lulu’s and Wrights in Manhattan Beach as well as Minnie T’s, Heist, and The Guild in Venice; and the awesome Jennie at Barneys in LA, where they call me as soon as interesting pieces come in and also send photos over if I ask. It makes my life so much easier when I am traveling a lot and I don’t feel that I am “missing” anything. Forty Five Ten in Dallas, does the same things for me and is always so welcoming when I pop by when I am on location out there. I really appreciate having awesome stores and fantastic salespeople who ‘get me’ and know what I like.”


ysl turquoise arty oval ring saks fifth avenue cindywhitehead interview candaceroseYSL Yves Saint Laurent – Arty Ovale Ring (in turquoise) –

minnie t's boutiqueOne of Cindy’s favorite boutiques, Minnie T’s – Minnie T’s (Venice & Culver City, California) – Minnie T’s Boutique


One Item Every Woman Should Own

Candie Anderson: What is the one item every woman should have in her closet?

Cindy Whitehead: “An awesome bag that makes you feel great when you carry it. Your whole outfit can be based around that one piece and even if everything else was just very simple pieces (or even sweats) the bag would pull it together.”


OffSetStyleEvery woman needs “an awesome bag that makes you feel great when you carry it.” – Cindy Whitehead; Photo credit – Ian Logan


186182_D94IO_1000_A-black-arena-giant-envelope-handbags-1000x1000Black Giant Rose Gold Envelope – Balenciaga

Thoughts On Trends

Candie Anderson: Is there one trend you wish would disappear?

Cindy Whitehead: “Not really, because trends go in cycles and what I loved years ago, I may hate now, but younger girls may be experiencing it for the first time and when I start to say I ‘hate’ some trend, some awesome girl comes along and rocks it like nobody’s business and I change my mind. Being open to new ideas and how people put things together is what I think fashion is about.”


Favorite Way To Unwind

Candie Anderson: How do you like to unwind in your free time?

Cindy Whitehead: “I like to look at blogs, fashion magazines, see movies, go to dinner, visit with friends and check out new and interesting stores. To me anything or anyone that inspires me is a perfect day!”


Cindy Whitehead Parker Hotel Palm SpringCindy Whitehead at The Parker Hotel in Palm Springs, California


Candie Anderson: Where can we go for more information?

Cindy Whitehead: “You can see my work at or stop by my blog and say ‘hi’ at”

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