J.Crew was one of the most beloved brands of the early aughts. But the preppy retailer fell hard and fast, filing for bankruptcy during the height of the coronavirus crisis last year. Many have been pontificating that the money moves J.Crew made led to the company’s $1.3 billion dollar debt. But in this case, it isn’t all about the Benjamins. The company failed to continue attracting customers during the recession. J.Crew’s 2020 bankruptcy comes down to the fact that the brand’s offerings didn’t reflect the cultural zeitgeist of the of the time.

But the company has made some financial headway since the bankruptcy. Axios reports that J.Crew shares have almost doubled over the last three months. Adding that, “J.Crew is now part of a shadowy group of retailers — including Neiman Marcus, JCPenney and Belk — that have gone through bankruptcy and now sit in a kind of ownership purgatory, with their equity held by a disparate group of former creditors.”

Designing its future, J.Crew is deviating even further from its signature style when it recently hired former Supreme designer Brendan Babenzien to “disrupt” the menswear brand. It’s a lot to digest. Instead of reviewing J.Crew’s many financial missteps, we’re going to take a look at where J.Crew went wrong in terms of branding, style, and cultural relevance –– and what it will take for the company to succeed in the future.

 A Little Background on J.Crew and Madewell

J.Crew is the definition of a legacy brand. The company’s roots date back to 1947 when Popular Merchandise was founded. Popular Merchandise launched the first J.Crew catalog in 1983 to sell low-priced apparel to the masses. The catalog offered a then-unparalleled trifecta of success: bargain-bin prices combined with high end photography/style guides and D2C apparel delivery.

[callout]J.Crew is reportedly going to retain its signature pretty menswear style, but is also giving Babenzien a lot of wiggle room for “creative flexibility.” But for Babenzien to be able to turn J.Crew around, his creative influence will need to extend beyond the menswear category.[/callout]

In the early aughts, J.Crew was a game-changer. Jenna Lyons was the controversial, revolutionary public face of the brand. She shook up J.Crew’s preppy fashions in womenswear –– popularizing bright colors, gender diversity, and sequins in the daytime.

Around the same time that Lyons was getting funky with the legacy brand, Madewell was added to the J.Crew portfolio. The public perception of Madewell is that it was founded back in 1937 by the Nozowitz family. But that’s not really true. The reality of J.Crew’s hip young offshoot line’s origin is that former J.Crew CEO Mickey Drexler bought Madewell’s logo and origin story when the original, family-owned Madewell shut down. This happened right before the recession in 2006, and none of the original team stayed on board when it became a J.Crew subsidiary.

But hey, if the brand’s story lures in millennials and Gen Z who would otherwise ignore the J.Crew band, can you really fault Drexler for finding something that works? While the acquired origin story worked for a time, the company’s About Us page is now focused on the quality of goods and the brand’s current designers, instead of the pre-packaged origin story.

The Schism Between J.Crew and Next-Gen Consumers

While J.Crew made gains during the recession, consumer sentiment began to change around this time. The brand’s preppy aesthetic just didn’t hold up in a world where uniqueness trumped conformity. The company’s high prices began to cause dissonance. Suddenly J.Crew’s luxe sequined blouses and detailed blazers felt unnecessarily lavish, not essential. Sequins during the daytime felt rude when so much of the world was unemployed. The brand was trying to sell goods at exorbitant price points right after the recession, and much of its core customer base began to stray to off-price stores and (at the time) micro retailers like Everlane that offered greater pricing transparency.

When Lyons left J.Crew in 2017, the company struggled to lock down a new signature style. The company rehired Chris Benz as J.Crew’s new head of women’s design. Benz was at J.Crew during its heyday and his approach harkened back to the preppy basics of the pre-Lyons era. But getting back to basics didn’t resonate, in this case. Benz left the company in 2020 and was replaced by another rehire: Olympia Gayot was previously on the design team at J.Crew, from 2010-2017. She was hired as the Executive Vice President of Women\’s Design at J.Crew. Olympia is now the one behind the helm at J.Crew Women’s, along with J.Crew Group CEO, Libby Wadle.

It also bears mentioning that J.Crew/Madewell continue to divide apparel categories into Menswear and Womenswear without any grey area. Remember when I said that “Gender Norms in Retail Alienate Gen Z?” Well, this has never been more true as young adults across the globe emerge from an introspective period of pandemic lockdown. PinkNews recently released a report that found that 56 percent of millennials and 50 percent of Gen Z consider the gender binary to be outdated.

Is There Skatewear in J.Crew’s Future?

Having filed for bankruptcy in May 2020, J.Crew was overdue for an overhaul. The company needed a new public face. It was oddly mum on the topic when Olympia was hired to replace Benz in womenswear. So, it needed a new celebrity designer to reel in next-gens by taking controversial style risks. Enter the New York born Brendan Babenzien, former lead designer for Supreme and co-founder of environmentally conscious menswear line, Noah. Babenzien is taking over the menswear category at J.Crew.

Babenzien was one of the original masterminds behind the iconic Supreme streetwear label. If you aren’t familiar with Supreme, you probably don’t have any fashion-forward next-gens in your life. The company was founded as a skatewear label, but it grew into a $2 billion luxury apparel and accessory brand. It’s known for limited edition product runs and highly hyped designer collaborations with skyrocketing resale values.

Babenzien has a strong artistic sensibility and knows exactly what it takes to create consumer demand. But can Babenzien prevent J.Crew from joining other heavy hitters from the early aughts in relative obscurity? That depends on the scope of his influence.

It’s hard to say how much of Babenzien’s signature rebelliousness will translate into his styles for the legacy brand. A recent article by the Wall Street Journal said that Babenzien’s vision for J.Crew would focus on “fundamental pieces echoing the clean-cut American look that the brand pushed in the 80’s and 90’s.”And that he “intends to place the brand’s no-fuss basics at the front and center again.” 

J.Crew is going to retain its signature pretty menswear style, but is also giving Babenzien a lot of wiggle room for “creative flexibility.” How Babenzien will be able to execute these two notions simultaneously is still a mystery, since none of his designs for J.Crew have been released. For Babenzien to be able to turn J.Crew around, his creative influence will need to extend beyond the menswear category… and they’re going to have to let him break some rules. His skatewear styles and his statement about creating callback preppy basics for J.Crew don’t align. Unless the brand is able to make use of Babenzien’s signature style, or they’re able to work together on a gender-neutral line, the legacy brand will be more disconnected than ever.

Looking Forward

It looks like Babenzien is already getting through to seasoned J.Crew corporate heads about how to create demand in a modern marketplace. Just look at the number of headlines he already stole when Babenzien’s J.Crew menswear designs won’t actually be available until the second half of 2022. Hopefully Babenzien will be able to combine the artistic collaborations and hypebeast product drops that Supreme became known for with the sustainability of Noah. But for Babenzien to be able to rescue J.Crew, the scope of his influence will need to extend to the menswear and womenswear category. This will take forward thinking and flexibility from J.Crew’s seasoned corporate heads. The verdict is still out on whether Babenzien will be able to execute the stylistic turnaround necessary to make the company relevant once again.

This report has been updated to reflect Olympia Gayot’s appointment as head of Women’s Design.