Similar to Karl Lagerfeld’s signature pony tail and Anna Wintour’s bob, like it or not, Jenna Lyons is iconic. Over six feet tall, often in form-fitting pants, bold costume jewelry and boxy, black-framed glasses, Jenna has not only mastered her signature look, she has also been praised by the New York Times as “the woman who dresses America.”

Recognized as an intrapreneur in spearheading multiple successful initiatives at J.Crew, Jenna joined the company after graduating from Parsons School of Design in 1990s at the ripe age of 21. She became the Head of Womenswear in 2003, before getting promoted to the role of President and Creative Director of the brand in 2010.

When you think things couldn’t get any better, America’s former First Lady Michelle Obama showed up in J.Crew for the presidential inauguration and then again on The Tonight Show with Jay Leno, giving the brand a significant boost.

Fast forward a few years and just as it was hard to envision the White House without the Obamas, it’s odd to imagine J.Crew without Jenna Lyons.

This past April, Jenna confirmed she will part ways with J.Crew after 26 years with the company.

What happened?

2003: Millard Drexler becomes CEO. Jenna becomes the Head of Womenswear. The same year, Millard buys the Madewell name.

2006: Jenna is celebrated for revitalizing the J.Crew’s brand by giving it a fresh new, fashion-forward look. Meanwhile, Madewell launches as its own denim label,

2008: The recession takes its toll on the fashion industry, but J.Crew remains hot. Michelle Obama wears a J.Crew cardigan on The Tonight Show with Jay Leno and gives the brand a big boost.

2010: Jenna is named President and Creative Director. Sales soften due to a lack of fashion hits and discounting by competitors. Rather than discounting, J.Crew strategically repositions by elevating its prices to reflect luxury status.

2011: Jenna becomes a fashion celebrity, making an appearance at A-List events, including the Met Gala. Under her direction, J.Crew’s womenswear collection grows in popularity.

2012: J.Crew peaks in sales. Rise of e-commerce and new players in fast-fashion means consumers are bombarded with promotions and are reluctant to buy at full-price.

2014: Sales slow down substantially. J.Crew reluctantly offers frequent discounts. Unable to remain competitive, the brand loses relevance with customers. On the other hand, the Madewell brand, led by Somsack Sikhounmuong is showing strong growth.

2016: Unable to turn sales around, J.Crew continues to discount; leading to shrinking margins and a deteriorated brand image.

2017: Jenna part ways with J.Crew by December. Her position will not be filled. Instead, Somsack will take over as the Chief Designer. A few months later, Millard also announced he will be stepping down. President of West Elm, Jim Brett, will assume the CEO role in July, beginning a new era for the company.

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What really happened?

Did Jenna lose her touch or was the fashion industry getting too competitive, even for its finest players?

The industry

At a time nearly all clothing chains are struggling, J.Crew must figure a way back into the hearts of their consumers. The rise of the digital era meant that beloved mall brands must now overcome the shoppers’ shift to discounting, fast fashion competitors like Zara and H&M, as well as made-on-the-internet brands like Nasty Gal and Everlane.


More recently on Jenna’s watch, there were fashion misfires, uneven quality and issues with fit and sizing.

Identity crisis

Part of the problem has to do with design. J.Crew’s offerings can be split into two categories: timeless basics and trendy quirkiness. Based on sales numbers, neither is serving the retailer well. Recently, the company’s designs have been criticized as “overpriced, eccentric, and even downright ugly.” The real problem? The company appears to be catering to the wrong crowd – the fashionistas at Fashion Week, rather than their loyal customer base and true fans.

The “J” in J.Crew does not stand for Jenna.

“I was a fan of J.Crew for over 20 years,” a customer tells The Post. “But as I look at the catalogs now, I just don’t get it. Back when I was in college, it represented a classic look that was seamless. Now, the brand embodies Lyons’ creative-cool lifestyle.” “I love her style,” she explains. “But can I relate to it?”

Jenna Lyons fashion


Empathetic but not apologetic, Jenna acknowledges the state of affairs at J.Crew’s. Persevering through the industry highs and lows and holding her head up during the good times and the bad, here are key learnings from Jenna:

There’s no such thing as overnight success.

Started out as an “assistant to an assistant to someone else’s assistant,” as she puts it, designing the company’s old-world men’s rugby shirts. “It’s taken me years to get here, and I’ve cultivated it so carefully,” says Jenna.

Stay true to your values.

She is grateful to her fans but refuses to be a slave to them. According to an article from Times, two weeks before the Oscars in 2012, Jenna received a request to dress a star for the red carpet. She turned them down saying “we can’t turn samples and make really good-quality clothes on such a tight timeline. I certainly love the idea, but we’re not set up that way.”

More than fashion

Jenna play a vital role in making upbeat colours and geek-chic patterns a staple in our wardrobe. She taught women how to dress without intimidating them or making them feel less than. Infiltrating beyond closets and magazine covers across the globe, Jenna has ultimately shaped fashion, what constitutes as beauty and pop culture as a whole.

J. Crew | NYFW with Jenna Lyons

What comes after the rise and fall?

“Jenna has been involved with J. Crew for over 25 years through ups and downs and has weathered challenges before,” Business Insider reports. Many are confident that both Jenna and the company will pull through.”

Moreover, Jenna’s talent didn’t just disappear. With a strong personality and a cool edge as a leader, intrapreneurs can become entrepreneurs and vice versa. “I’d love to see her do her own brand and take it to another level. She’s a visionary,” says a close partner of the company.

In sum, with the highs come the lows. Essentially, mistakes are inevitable; we’re human after all. Failures don’t define us. Rather, it is how we bounce back that helps define who we are as a person. Speculating what Jenna will do next? Thoughts on this post? I’d love to hear from you!