Life & Businessproducts

An Interview with Stylist Ayanna James

by Grace Bonney

For my everyday life, I’ve pretty much winnowed down my wardrobe to a small amount of trusted pieces (mostly in grey and black). And as much as I love my unofficial uniform, there’s always a little part of me that wants to get all dolled up with the help of someone who knows what they’re doing when it comes to fashion. I’ve always admired stylists and fashion designers because they have an innate sense of what works on someone and how to make them feel comfortable and confident at the same time. So this week, I thought I’d reach out to a stylist, Ayanna James, who I’ve admired for a while after discovering the work she’s been doing with Issa Rae on her upcoming HBO show, Insecure.

Ayanna has come a long way since starting her career in fashion in 2009, and has gone from launching a fashion blog with her friends to styling some of the biggest names in music, movies and sports. Ayanna gets to have one of my dream jobs, too — working with people who walk the red carpet. The glamour and the magic of it all is so exciting to me, but I wanted to hear about the business and day-to-day work behind such a high-profile job. So today, Ayanna is joining us to talk about her path to being a lead stylist and what it’s like to design and style wardrobes for a range of different events. Thanks so much to Ayanna for joining us today! xo, grace

Can you remember when you first learned about your field of work?

By the time I discovered what a stylist actually was, I had been doing it for a while. I did my first pull in high school, without even knowing what it was. The Academy Of Finance’s senior program put on a fashion show every year and I thought it was so cool. When I became a senior, I signed up to help put one on. I was in charge of the “Hip hop” and something else. It was lots of fun and that’s all I really cared about. We had to approach stores and boutiques and ask them to sponsor clothing. I had to do fittings and choose the models. I had no idea people actually did this for a living until I was in my last year of college.

How did you discover what it was and how you knew it was what you wanted to do?

I grew up pretty conservative. My father wasn’t into name brand clothing or style. I never really saw myself as a stylist. It wasn’t until I was a junior in college [that] I realized I had style. I was studying biochemistry and worked as a store manager, full-time, at American Apparel. I opened their Washington Ave store. The cool thing with AA back then, was Dov Charney really allowed the store managers to curate their own inventory. Much of the clothing in AA were ideas from the employees. We listened to customers and gave feedback on our weekly conference calls. I was really inspired by his willingness to allow us to help build the brand. We were located on South Beach. Celebrities and socialites were always coming into my store asking for help to find something to wear. They would look at me and say “I want that outfit.” My best friend and I had a different style compared to the rest of South Florida, so we got a lot of attention because of it. It was at this point, I had my “ah ha!” moment.

When did you decide that this was the job for you?

I think the Universe decided it for me. I kept stumbling into really cool opportunities, but because I didn’t have a background in fashion, I kept referring to it as a hobby instead of calling it a career. It wasn’t until a friend of mine encouraged me to pursue styling. If it wasn’t for him I would be knee deep in bacteria cultures (chuckles).

What was your path that lead you to the job you have now?

I was in Miami studying, feeling unfulfilled. My family moved to Los Angeles and when I told them I wasn’t sure Biochem was for me, they chocked it up to me being burnt out. I came to LA for what was intended to be just the summer, but ended up staying after being in a serious car accident. It was just more convenient being close to family. During that time, blogging was really popular and I remember seeing Karla’s Closet collaborate with Coach. When I looked at her site, I realized the importance of style and its relation to influence. I thought to myself, “I have style. Why aren’t I being paid for it?” So I started a blog with 5 of my college friends. We had a direct network of readers because of my time at Florida A&M University. I wanted to speak to them. As time went on, the blog grew in subscriptions and I was taking off work because of the workload and opportunities that came with it. I started to set up my own work schedule outside of work. My friend encouraged me to pursue styling and I fought it. Hard. It wasn’t until a really big stylist tweeted “Ugh, I need an assistant,” that things really got interesting. I took a chance and responded to her tweet and emailed my resume. She interviewed me and hired me on the spot.

Why did you decide to start your own business, versus work for someone else?

About four months after assisting this stylist, she fired me. I was devastated. I thought I would work with her for two years and then branch out on my own. But she wasn’t really feeling me. During those four months, however, I did a lot. I styled many of her clients and got a good enough understanding of how to do it myself. I reached out to anyone I knew in the industry and showed them the work I had done with her. A week after being fired, B.o.B’s manager, TJ Chapman, reached out to me and asked me to style B.o.B for the VH1 awards. I had like two hours to shop, but managed to pull it off. That was the first time I sent my own invoice to be paid.

What was the best piece of business advice you were given when you were starting off?

“Do the work.” It works for both your personal and professional life. Don’t cut corners. People appreciate when you over-deliver and most times they’ll be the ones to refer you to someone else.

What was the most difficult part of starting your business?

EVERYTHING. Mostly, not having many contacts. Not knowing photographers, or producers or anyone who didn’t have a regular job. It’s a blessing I moved to LA, because everyone is literally one degree away from someone who can put you on. You just have to put yourself on first.

Can you name the biggest lesson you’ve learned in running a business?

Patience and persistence. So many times I wanted to give up. I would look at other stylists and wonder “What am I doing wrong?” But I had to be patient. I had to wait my turn and do the work. You can cheat the hustle. It always backfires. Every time I finish a job, I struggle with depression. I’ve had to learn to balance life and work. Finally, as I near 30, I think I’m starting to get the hang of it.

Can you name a moment of failure (or when something didn’t work out as expected) in your business experiences that you learned from or that helped you improve your business or the way you work?

Every experience has its pitfalls. We are our own worst critic. I look at my work over the years and cringe at some of it. But at the time, I thought it was great! In wardrobe styling, there is never enough time or resources to do it all. You have to take your wins with your losses. I take every moment of failure or disappointment to make myself better.

If you were magically given 3 more hours per day, what would you do with them?

Work out. I haven’t had the time to exercise in a while. 12-hour days on set leave you drained and all I want to do is sleep.

What has been the biggest sacrifice you’ve made in starting your business?

In the beginning, instability. I would go weeks with a very tight budget because an invoice is late or a job was canceled. You’re still getting your feet wet and learning a lot. It’s like a baby learning to walk – you’re going to take some tumbles.

Can you name your greatest success (or something you’re most proud of) in your business experiences?

Most recently I wrapped a pilot for HBO named Insecure, written by and starring Issa Rae. I’ve been working with her for a while and I’ve seen the work she’s put in. She’s amazing. She works HARD behind the scenes for indie writers of color, especially women of color. I love her for asking me to be a part of her project.

What’s the first app, website or thing you open/do in the morning?

Whenever I pick up my phone in the morning, I just go through all of my notifications. I’m addicted to Instagram. I wake up around 5am every morning, I’ll lay in bed for about 30 minutes and play around on my phone. After, I go through yesterday’s to-do list and transfer the things I didn’t complete to today’s list and add on whatever the day calls for. Then I start checking things off.

Where do you go when you need inspiration for your work?

Travel. I love to travel. I’ll hop on a plane and go anywhere (warm). I’ve always been that way and so is my family. I attribute much of my creativity to the experiences I’ve had.

What’s the hardest thing about being your own boss that isn’t obvious?

Staying centered. Not too high, not too low. Freelance life can be tough at first. Especially when you take the jump to full-time. Delegating, sometimes I can be micromanaging, I like to feel and touch every piece of clothing before it steps in front of the camera and sometimes there just isn’t enough time.

All photos courtesy of Ayanna James


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  • Amazing read! She will go far as it seems to be not only her passion but her lifestyle. Wish her nothing but success and will definitely keep an eye on her as she continues on this awesome journey!

    • Definitely. Also about learning to enjoy the process. Now I no longer have anxiety when faced with challenges.

      Thank your for reading!

  • Thank you for interviewing Ayanna, Grace. You cover so many fun, creative people, it’s perplexing why you wear, as you called it, a “uniform” of grey. That’s what struck me about the picture of you at the White House with Michelle Obama: why is Grace wearing a grey uniform looking blazer? Why? That’s not a criticism, just curious.

    • Ruth

      Because that’s what I feel most comfortable in, plain and simple. I’m inspired by all sorts of people, people who embrace color and pattern and people (like one of my idols, Eileen Fisher) who can make dressing in neutrals seem so chic and timeless. Much like all of us who admire and read about creative people online, I don’t necessarily dress the same way that they do. I’m surprised and a little saddened that what I was wearing is what you took away from that story on the White House.


      • Oh gosh no, I took waaaaaay more from your story on the White House! I was just curious because it seemed like there would a hundred stylists ready to dress you for such an event :) Thanks for your inspiring coverage of really creative people.

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