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Sarah Clary

Stylist Sarah Clary grew up in Northern California, a place she acknowledges “isn’t necessarily known for its high fashion.” While her narrative isn’t unfamiliar (“I often felt like an ugly and gawky kid — too skinny and not pretty enough,” she says), what cuts through is that she used clothes to express herself from a young age. Clary recalls keeping track of styling hits and misses, challenging herself not to repeat looks twice. In many ways, she was developing skills for her future job without realizing it.

Sarah Clary

Clary has worked with brands like GAP Kids, Kule, Old Navy, Burberry and, of course, J.Crew,  where she first met Mickey Drexler and Jenna and where she led styling for crewcuts, the beloved kids division. Clary often teams up with photographers like Annemarieke van Drimmelen, Roman Coppola, Coliena Rentmeester and Mei Tao, whom she also calls friends. We caught up with Clary to talk about working with Jenna way back when, the first piece she ever splurged on, and why a tulle skirt on top of a mountain is a totally acceptable wardrobe choice while on set.

On what brought her to New York

I came to New York with big fashion dreams but little skills or connections. Out of college, I got a job at J.Crew — it was my dream to work for Mickey Drexler, a retailing legend in San Francisco. I started on the business side but quickly knew it wasn’t for me. After a few tough years spent behind a desk, I decided to move on, and while I wasn’t sure exactly what I wanted to do, I felt creatively pulled to find my place within the industry. During my exit interview, J.Crew’s HR department mentioned that Jenna Lyons had noticed me and was curious if I wanted to move into the styling department as an assistant. That was when my life changed.  She saw me and gave me a chance, and she has been doing that ever since.

On working with Jenna during the J.Crew years

I have been many things under Jenna: an assistant, a freelancer, a collaborator, and a friend. In every role, she has made me better and shown me my strengths, and helped me learn from my weaknesses. She is a creative genius who can uniquely capture, embrace, encourage and share beauty in often-overlooked spaces. She sees talent, and she pushes you to see it in yourself. I have learned and continue to learn so much from her, and I am forever grateful for her confidence in me. From the day she didn’t let me quit J.Crew to the day she supported my freelance career to the day she pulled me into her life after J.Crew, she has consistently been in my corner, and I will forever be in hers.

On the professional challenges of being a stylist

It is always about making people feel good. Full stop. That never gets old. As a stylist, you have the ability to transform someone’s mood or how they view themselves. I love the collaboration that is required to make a photo or commercial come to life. It’s never just one person who makes a vision come alive, and I’m humbled by the talented people I have met through the years that have helped me be better or see beauty in a new way.  

As a freelancer, the hardest part is the feeling of floating. I love the flexibility that freelance provides — time off and new job opportunities that come up from week to week — but it’s easy to feel like you’re on an island without a team to lean on for support and guidance, too.

On her personal style

I still use clothing as my armor. My personal style changes based on how I want to feel — even if I am faking it. I’m always attracted to a great blazer, tulle skirt or a stripe. Whether it’s tomboy or girly, I’m game.

On the first piece of clothing she splurged on

After leaving my full-time job at J.Crew, I took a risk and started my now-long career as a freelance stylist and consultant. I was terrified I would never make money in this industry full of so many talented people. When I booked my first fashion campaign with real money, it was a humbling moment. I went to Miu Miu and bought myself a beautiful embroidered coat and paid full price. I still have that coat as a reminder of all my hard work.

On dressing up

Don’t let the good things die in your closet. Don’t save them for that event you may never go to.  I’m a working mom with no place to go, but I have worn a tulle skirt on top of a mountain while working, or a sequin dress to pick up my kids. Clothing makes me feel good, so I try to not let those feel-good pieces collect dust.

On setting the record straight on a fashion misconception

Dress your age. What does that mean? I was pretty shy and dressed more conservatively when I was younger. Now that I’m older and have two kids, I feel more comfortable in my body. I’m sad it took so long to realize, but now I let it all hang out. I’m thankful for a body that still works every day, so I’m leaning into that.

Want to see more? Watch Stylish with Jenna Lyons on HBO Max.