How I Became... A Stylist

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LOS ANGELES, United States — Born and raised in St. Louis, Missouri, Jason Bolden's midwestern upbringing initially obstructed his understanding of a career in fashion. However, after moving to Chicago to study pre-med at Northwestern University and blowing his funds in the first week, Bolden took a retail job at Cynthia Rowley, where he discovered the fashion industry was "bigger than just putting clothes on people and walking them down the runway."

While studying in Chicago, Bolden continued working at luxury stores like Louis Vuitton, Gucci and Oscar de la Renta, where he began building up a client list. Bolden later moved to New York, where he opened a vintage store in Soho called The Garment Room, which curated vintage collections.

Gabrielle Union, an actress and friend of Bolden's, asked him to style her for the for-profit art fair Art Basel in 2011 — "then the phone calls started rolling in." Today, the celebrity stylist counts among his clientele actresses Taraji P. Henson, Sasha Lane and Yara Shahidi, rapper and actor Wiz Khalifa, as well as athlete and entrepreneur Serena Williams. In 2017, he was recognised as one of Hollywood Reporter's "Top 25 Most Powerful Stylists."

Bolden has also acted as a red-carpet commentator for E! and co-founded JSN Studio, a multi-disciplinary design studio in Los Angeles, with his partner Adair Curtis. Here, he shares his career advice.

What drew you, and held you, to a career in fashion?

I’ve always gravitated towards fashion because of my grandmother, who had a distinctive, classic but relaxed luxury approach to lifestyle and clothes. But coming from the mid-west in the US, fashion and working in the arts was not promoted. The idea is that you become a doctor, an attorney, a teacher, an engineer; the classic jobs that people have examples of success from.

I went to school in Chicago to become an obstetrics gynaecologist and my mum gave me a credit card with $500 on it, which I had to stretch out — but I blew it the first day on a backpack for school. That first week, I was like, “How am I going to eat?” So, I ended up getting a job in retail at [lifestyle brand] Cynthia Rowley. I just remember loving clothes — I couldn’t wait for new deliveries to hit the store. It was a personal, intimate connection with clothing.

My struggle was being a black man in fashion, where you were never seen or heard — today, there are moments when that still exists.

When I worked at [womenswear brand] Nicole Miller, I had my first celebrity styling experience — but as a college kid collecting money to hang out with my friends. It wasn’t about trying to build this career. It was a country singer called Martina McBride and I was helping her over the phone. From there, I went to [work as a retail assistant at] Louis Vuitton, Gucci and Oscar de la Renta, [where I continued to assist specific clients] but still never knew that styling or creative direction was an option for me.

When did you realise, and start pursuing, styling as a career?

One summer, I moved to New York and opened a designer vintage store called The Garment Room where we collected designer vintage [pieces]. It was one of the first pop-up stores in Soho and it created this really cool buzz. We were taking an old Valentino dress and bringing the hem up or taking a Courrèges jacket and flipping it inside out. People from Ralph Lauren, Philip Lim, Acris would come to the store and buy items to create sweeps to get design inspiration from. It was another experience of realising that the fashion business was bigger than just putting clothes on people and walking them down the runway.

Then, one day, I got a phone call from a good friend, the actress Gabrielle Union, and she said to me, “I need something to wear to Art Basel [in 2011], can you please bring me something from the store?” I brought her this quintessential, 1970s Lanvin print and a classic black Alaïa dress from the late 80s. She wore it to a party, and the next day, there was an article about her look. Then the phone calls started rolling in.

I had always loosely been styling with private clients but I never looked at it as styling. I love beautiful things and I wanted to place beautiful things on beautiful people — I didn’t realise I was styling. Then it all fell into place from there.

What qualities made you stand out in your first job?

I was very ambitious and I had a lot of tenacity. There is also something about presenting my clients with clothing that makes me just innately happy. It transcended beyond just putting clothes on people, which stood out to [my clients]. I was always super excited about being in the room and being surrounded by those beautiful clothes. Sometimes, people can’t help but fall in love with your passion and that’s helped me through my journey.

How can you access industry insight while living outside a fashion capital?

What’s amazing right now is that you can be anywhere [and pursue a career in fashion] due to the resources that we have now. With social media, you are able to connect with people and see things that you never thought you’d be able to see. You have everything at your fingertips.

All you really need is one yes and you take that one yes and transform it into a million yeses.

Being in the mid-west was great because it meant I got a different perspective. But when I moved to New York, that was where everything was based. If you wanted to work for a major magazine, it would have to be there. If you wanted to do an internship at a major fashion house, it would be there.

What has been the most challenging aspects of your role?

The most challenging aspect for my role was being a stylist of colour. When I first got into the business, it was tricky. It didn't feel warm and fuzzy at all. My struggle was being a black man in fashion, where you were never seen or heard — and today, there are moments when that still exists. But I worked with such amazing, culture-shifting people who I never needed validation from. When it didn't feel warm and fuzzy, I could go back to my clients and I got what I needed.

Truly, you only need one yes. And if someone was to tell me that a long time ago, it would have helped me. I wouldn’t have had so many emotional breakdowns or looked at myself as not worthy. All you really need is one yes and you take that one yes and transform it into a million yeses.

What advice would you give a junior starting out today?

The biggest thing is to do your research. Study to discover. Learn as much as you can. I sometimes thought I knew more than I did, and I didn’t take enough time to sit down and do some research. But you can never take in enough information. I research designers, artists, architects — I go across the board. The more you know about things, the more you can connect them to your ultimate passion. You are then able to understand and have a full conversation about anything.

I would also go to the locations where everything is happening and just hang there. Make friends. I made friends through retail and I would be introduced to so many different people. Plant yourself in a place where you have no choice but to constantly be intertwined with people you want to be in that business with.

The other thing is figuring out if there is someone that needs assistance, even once or twice a week. I know in my business, there is always space for someone to come and help. Don’t be afraid to actually put yourself out there and ask anyone if they need help or assistance.

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