Ones To Know:: Cindy Whitehead – SportsStylist®

Over the last few years I have been fortunate enough to meet and interact with some amazing women blazing the trails in their respected careers.  I am all about empowering women as sadly that is not always true for others, and decided to start featuring “Ones to Know” in a new column and share with all our readers.  We are launching this segment with Cindy Whitehead, renowned SportsStylist® all around amazing person.

Photo Credit: Ian Logan

You were one of the first women professional vert skateboarders. How did you transition from professional skateboarder to stylist?  When did you decide to specialize in sport styling?

I always had thoughts on what I wanted to wear when I was skateboarding. From my shirts and shorts down to the color ways on my sneakers. It wasn’t just about what to wear for a photo shoot, or when I was competing; it was an everyday thing for me. So I suppose it was a natural progression to end up here doing fashion styling. But since I didn’t have any idea this career even existed back then, I took a few detours on the way delving into TV/Film production, working in the photo department at Mattel Toys, among other things. When I was at Mattel I got into trouble for styling a Barbie w/a risqué swimsuit (by their standards) I had “designed” and hanging her above my desk I knew at that point I had found what I wanted to do. After that “enlightening” experience I went to work for a swimwear magazine & manufacturer in San Jose, CA and started styling all their editorial and catalog shoots all over the world. From there I came back home to the LA area, got an agent and started breaking into advertising shoots as well. I also did a little bit of the “celebrity” styling thing – working on shoots with Tiffany Amber Thiessen, Greg Kinnear, Billy Baldwin, Lyle Lovett, etc. etc. I also styled MK & Ashley and Angelina Jolie back when they were literally pre-teens.

I met a photographer through my then boyfriend (now my husband) who was doing all sports shoots (which was unusual at the time) and started working with him a lot. During that time I met another photographer who was also delving into that scene and decided this was the direction I wanted to head. It fused my two loves together to make a prefect career for me. So I spoke to my agency and let them know this is where I was headed and the response was not good. So I chose to follow my own path, & do it on my own. I later trademarked the name Sports Stylist® and here I am. You really have to do what you love.

What’s the best styling trick you’ve learned from all of your years of experience?

Well it’s not really a trick, but I would say that you never want to send your model/actor/celebrity/athlete/ etc. out the door onto set or the red carpet in something they are not comfortable in (even if you love it) because they will never look/feel comfortable and regardless of how great the look is. It literally shows in their body language and the look goes from being “amazing” to being a “don’t”.

Where do you draw inspiration, when you’re styling and working?

I tend to find inspiration from everywhere. If you follow me on instagram (@sportsstylist) you probably already know that I am pulling ideas from my surroundings all the time. I find it all inspirational – from graffiti to street style, to nature. It all jumps out at me and makes an impression. I find new experiences, places, people and things highly motivating – it keeps my senses alive and the creative juices flowing.

Photo Credit: Nike/Steve Bonini

We love your new Blog, what was the thought process behind it?

Thank you so much! When I was on Blogger I got censored for having a photo up of an edgy looking model with a nipple exposed and I had to beg to get the “warning label” lifted from my site. Right then I knew that I was going to need to host my own site at some point. I also started feeling like most of the blogs I was looking at were all very pretty and while I enjoy that, I realized there wasn’t a lot out there that was in your face and edgy. I figured if I felt that was lacking in the blogging world, then maybe others were wanting it too.  So I guess maybe I thought it was time for some anarchy.

I was busy with a lot of other big projects but kept filing away ideas and notes on what it would be like if I made it what I really wanted and I finally sat down and reached out to an old skater friend, Judi Oyama (Maximum Impact Design) who does amazing graphics, and asked if she would design it and be a part of it. She jumped right in and started churning out some insanely rad ideas immediately. Judi is me in a sense, she grew up in the same world I did skateboarding and living with the boys on tour, so she knew what I was going for with “It’s Not About Pretty”. On the other hand I have no filter and probably do/say things she is smart enough not to. So we make a good team – I encourage her to fully let loose with anything she designs for me and she reels me in when I get too far out there.

Another intracle part of this design process/team is Carrie at Sweet Faerie Designs. Carrie also let loose designing edgy & amazing elements/graphics you see on the site like that  “Lets Pin This Bitch” button that shows up when you scroll across any post so you can pin each photo directly to Pinterest.  She is another one who when I get a crazy ideas just goes for it and try’s a million solutions to make it happen and when she comes back to me it’s even better than I imagined! She always adds some sort of rad twist to my ideas and I literally suck in my breath because it’s always perfect. And can we also talk about the fact that she is a coding genius? Getting my Skate x Fashion movie to play directly on that movie screen (on the Posse page) was something I was told numerous times by people in the industry that could not happen due to each computer having a different screen resolution/size/browser blah blah blah… Carrie found a way to make it happen. She refuses to take “No” for an answer. You see what I am saying?

My badass husband Ian Logan, did all the photography you see on the site. I drove him nuts having him do very specific photo shoots for various sections. A prime example is the “Stalk Me” page. I wanted a gritty mens bathroom stall but I needed an open area with a metal (not a concrete wall) to hang the skateboard on. The dude totally scouted numerous bathrooms for me finding the perfect one. When we went to shoot it, it had pee all over the floor, it smelled disgusting and I had to hold my breath while we shot. All he ever said as he was down on the gross ground shooting various angles was “you wanted gritty…”. Gotta love him.

How has the industry changed in the past few years with the introduction of social media?

I think the photography/hair & make-up/ styling end of my industry has changed a lot. Most of us get jobs based on our portfolio websites now (rather than showing a actual hard portfolio that we used to send out or show in person) and I actually now have clients asking me to tweet, FB or instagram  about the shoots we are on – less and less is “under wraps” like it used to be. Clients understand the importance of social media and creating some “buzz’ for a new product before it actually launches. I think what is important though, is to remember that we need to back up our claims when we post on social media, in other words it’s not enough to list your profession as x, y, z – there should be a website etc. to back it up. I find that there are a lot of people using Social Media “saying” they are something that perhaps they are not. That’s something that was harder to do/get away with back in the day.

You are writing a digital and social media column for Workbook.  How did that come about?

I have been involved with Workbook ever since I got started in this business. It’s always been the resource “bible” for our industry – from photographers to production crew. But until recently, the production team people (hair, make-up, stylist, CGI, producers, location scouts, etc.) have only had written listings, but in the past year or so Workbook has added online portfolios to their base for us, which is great! You have to be vetted to be able to be in Workbook so the great thing about it is, you know everyone listed is a working professional at a certain level.

I started talking to them about social media and it’s importance and then Lorena who is my point person there, suggested to the owners that I be a regular contributor to the site. A lot of professional advertising photographers are very hesitant to use/embrace social media, so I think that the Workbook people thought if it’s “basic” info coming form someone who knows this end of the industry and is using it herself, and can say what’s good/bad, maybe it can help?

What are your top 3 tips for photographers and stylists on how to better utilize social media for their businesses?

  1. Be consistent with your postings – this does not have to mean posting every day but it also doesn’t mean once a month
  2. Respond to tweets, FB posts etc. It’s like returning a phone call, if you think of it that way you can’t go wrong.
  3. It’s not always about promoting your business and if you do that you will have people lose interest. And it becomes boring… And no one likes boring!

Photo Credit:  K-Swiss/ Photographer Embry Rucker

What’s your favorite purchase of the season so far?

Just one?? Lol An amazing and large shark tooth Necklace by Heather Gardner, a sparkly peace sign boho chic bracelet by Lost Bird Designs, a bad ass Givenchy studded cuff, an Isabel Marant dress and the coveted Chloe “Suzzane” boots. Don’t even ask me how I pulled off nabbing those!

Your most memorable career experience?

Being at the Teen Choice Awards with my client, World Champion & Olympic medalist ice skater, Michelle Kwan (who won for best female athlete that year) and at one point during the evening INSTYLE MAGAZINE was interviewing her and asked her “What is your favorite fashion accessory?” and she told them “my stylist, Cindy Whitehead”. It blew me away.

The one thing in your closet that you will never part with?

The amazing pieces of jewelry that my husband has gotten me over the years.  And maybe all the Rick Owens pieces I have amassed. (-:

Three words to that describe your style.

Bohemian, Edgy, Rocker

Photo Credit: Wrangler / Mark Scott

What are your tips on building a successful business as a woman entrepreneur?

1. Listen to your gut no matter what anyone else tells you.

2. Giving compliments to other women in business never takes anything away from what you are doing – it only builds all of us up.

3. Jealously is a wasted emotion, I prefer envy.  I feel that you can be envious of someone else’s accomplishments and continue to appreciate them while working hard to build your own.

4. Go out into then world and kick some ass! It’s really that simple.

Cindy Whitehead – Sports Stylist®, created a niche as a wardrobe stylist that specializes in dressing athletes and models for athletic based ad campaigns, commercials and editorial spreads. Expertise in finding the appropriate apparel and gear for any sport necessary. Strong relationships with PR firms to pull for editorial. Numerous long term relationships with athletes and their management teams ensure that the shoot runs smoothly. She has gained respect from some of the top names in sports as being understanding of the athletes needs as well as the clients. Her philosophy is “keep it authentic”. To learn more about Cindy, visit her website and blog.