enna Lyons is like the high-achieving, impeccably dressed best friend everyone wishes they had - or themselves aspire to be. For one thing, she gets up refreshingly late. She tells Harper’s Bazaar, “I wake up as late as I possibly can. The first thing I do is hit the snooze button. I love the snooze button—it's really a drug. I give myself maybe half an hour before I have to be out the door. One of my assistants gave me a T-shirt that says SORRY I'M LATE.”
But Jenna Lyons has earned that right. Having learnt to sew in a home economics class, she started out designing and making her own clothes when she found it difficult to find items to suit her exceptionally tall teenage frame. “I remember going to school and it was the first time anybody paid attention to the way I looked,” she tells Stylist. Anyone not paying close attention might think that her success came quickly after that, but that’s far from true. Lyons says of her success: "It's taken me years to get here, and I've cultivated it so carefully. But I didn't think it was possible. I just assumed I'd plateau and that there would be no place for me to go."
She started at J. Crew at age 21 after graduating from Parsons and began her career, as she puts it, as an “assistant to an assistant to someone else's assistant” with a position so low that her desk was in the corridor. However, her hard work and steady dedication paid off. By 2003 she was Vice President of Women’s Design. Then, in 2008, she became the brand’s Creative Director and in 2010 she was named President by CEO Millard “Mickey” Drexler.
Her dual role as president and creative director highlights Jenna Lyons’ rare skill combination: her keen eye for design and sharp business acumen. Back in the early 2000s, J. Crew was far from the fashion forward powerhouse it is today. Management consultants were dictating design and there was little room for innovation. It was then that Lyons, backed by Drexler, had the courage to turn J. Crew on its head and bring to life designs that spoke to her view of the brand. She became an advocate for the use of high-quality fabric and putting creative and colourful twists on preppy basics, an aesthetic that would earn J. Crew the brand loyalty of First Lady Michelle Obama and her the title of 'The Woman Who Dresses America' by New York Times in 2013.
The brand’s overhaul didn’t stop at just the clothes; Lyons felt that J. Crew stores were in dire need of refurbishment. However, convincing the powers that be to release the cash she saw as vital for the rebranding effort was another story. “It's hard when the finance team is used to putting a light fixture in the store that costs $2,000 and I'm like, 'Well, I want an $8,000 fixture,” she says. The image makeover was extended to J. Crew’s corporate headquarters as well as its website and even the famed catalogue - which is now called the J. Crew Style Guide. At J. Crew, Lyons says, “... no financial decision weighs heavier than a creative decision. They are equal."
A style icon in her own right, her Lyons lives and breathes her brand’s high-low look and masters its effortlessly chic aesthetic. She claims to only have two go-to looks, the smokey eye or red lips, but her trademark look is no doubt a bold lip and her now iconic geek chic dark-rimmed glasses. However, she insists that she doesn’t do uniforms. “The idea of a uniform is like a slow and painful death to me. There is nothing I like more than getting dressed.” This sentiment becomes even clearer when she describes her own closet; a fashion wonderland fit for a couture princess, with an entire bedroom having been converted to accommodate it. Though it seems an entire bedroom is needed; what with Jenna’s weakness for shoes she admits to owning easily over 300 pairs.
When it comes to fashion, Lyons straddles the line between the classic and the exciting. She tells Vogue, “There is a subtle shift where familiarity can feel tired and fresh can feel naive. With clothing and beauty, the one common element is timelessness.
Lyons is enviable in other ways too. She’s a shopping addict who collects luxury underwear, keeps a freezer stocked with ice cream and enjoys cocktails and rose champagne. She also she seems to have the whole work/life balance thing down to a perfect science. She makes a point of taking her young son, Beckett, to school every morning and tries to leave the office by 6 pm to have dinner with him.
As one of fashion’s most successful women, Lyons has a few words of wisdom for anyone wanting to climb the career ladder. Rather than having a list of accomplishments and to justify another list of demands, Lyons suggests you make yourself indispensable and find out how you can contribute. “Ask questions: “I’m ready to take it to the next step. What is it that I can do better?” That, to me, is an engaged, collaborative way to get somebody to the next level.”
Words by Minerva Jacquier