Once the go-to brand for Michelle Obama, J. Crew has been a staple of the American fashion landscape for decades but in recent years it lost its footing. Now, with almost 500 stores worldwide currently shuttered by the coronavirus pandemic, J. Crew Group Inc. – which operates J.Crew and Madewell – filed for bankruptcy on Monday. Reporting a $78.8 million net loss during its most recent fiscal year and burdened with more than $1 billion in debt, J. Crew’s fall shouldn’t come as a surprise. But to see the brand – a mall mainstay across US – reduced to this position still comes as a shock. According to CEO Jan Singer (formerly chief executive at Victoria’s Secret), the move is part of an “ongoing process to transform our business with the goal of driving long-term, sustainable growth for J.Crew and further enhancing Madewell’s growth momentum.” J. Crew Group started as Popular Club Plan in 1947, a door-to-door business that sold inexpensive women’s apparel. In 1983 the company relaunched as J. Crew, a catalog-only retailer, and positioned themselves as a cheaper alternative to Ralph Lauren. The first J. Crew store opened in 1989, in Manhattan, selling cheery American prepwear. But it was about ten years ago that J. Crew really hit its stride – changing its image from comfortable to chic, and becoming an inescapable part of the fashion landscape, from magazines and style blogs to the everywoman’s wardrobe. Under the stewardship of CEO and chairman Mickey Drexler (now chairman of the athletic apparel brand Outdoor Voices) and Jenna Lyons, who took over as creative director in 2008 and was promoted to president two years later, J. Crew came to epitomize a certain type of recession-era elegance. Inspired by Lyons’ own signature mix of casual designs and high-end pieces (she famously wore a feathered ball skirt and a slouchy beige sweater to the 2011 Met Gala), J.Crew sold pastel button-downs and perfectly draped T-shirts; sequinned blazers and oversized costume jewelry; jacquard trousers and distressed jeans. Poppy campaigns fronted by Joan Smalls, Sasha Pivovarova, Amber Valletta, Lauren Hutton and other top models provided social media fodder. Lyons’ approach was so widely embraced that, in 2013, the New York Times dubbed her “The woman who dresses America.” The brand offered a more accessible kind luxury. Celebrities like Jessica Alba, Blake Lively, Gwyneth Paltrow (a 2012 campaign star) and Reese Witherspoon were often spotted out in their J. Crew best. But their most influential celebrity fan was Michelle Obama. Mirroring Lyons’ high-low sensibility, Obama seemed to have the brand in constant rotation during her term as First Lady – J. Crew leather gloves were paired with a lime Isabel Toledo ensemble at her husband’s 2009 inauguration, a salmon skirt and sweater were worn in the pages of Vogue, pink pumps complemented a brocade dress by Tracy Reese at the 2012 Democratic National Convention. Her influence led to both sold-out stock and stock market boosts: In a 2010 study, New York University professor David Yermack found that J. Crew’s stock increased 25% after Obama wore J.Crew on “The Tonight Show” in October 2008. But J. Crew has struggled to maintain that level of covetability in recent years, as once-devoted shoppers bemoaned the brand’s increasingly eccentric designs and ever-climbing prices. In 2017, Lyons left the brand and was replaced by Johanna Uurasjarvi the following year. She was quickly replaced by Chris Benz, who was hired in early 2019. Neither was able to reignite interest in J.Crew. Today, both Lyons’ once-profitable eclectic preppiness and the brand’s original argyle sweaters and prim chinos seem from a different time. In an era of gender-neutral dressing, streetwear and – more recently – lockdown loungewear, it appears trends and shoppers have moved on and J. Crew has not. Unfortunately, irrelevance comes at a high price. J. Crew is the first major US retailer to declare bankruptcy during the pandemic, and it is not clear how many of their stores will reopen.