Woman wearing mask walks past J. Crew store that's window says Wang Ying/Xinhua via Getty

J. Crew has gone through a lot over the past 20 years.

In its heyday in the 2000s, J. Crew gained a reputation for being one of America's most recognizable brands, thanks to it's ability to toe the line between cool and pretentious.

A series of product gaffes and a failure to keep up with where the retail industry was headed led to sliding sales, management challenges, and eventually, bankruptcy.

J. Crew is hoping fresh design talent and a new CEO can restore its position. The company rose to prominence and fell from grace.

A J. Crew catalog from 1998 shows two people snowshoeing
A J. Crew holiday catalog from 1998.
James Keyser/Getty Images

The Popular Club Plan was founded by Mitchell Cinader.

The J. Crew catalog was launched six years later in New York City.

The brand was bought by a private equity firm in 1997.

Michelle Obama J.Crew
Malia and Sasha Obama are seen wearing coats from Crewcuts by J.Crew in 2009.
AP Photo/Chuck Kennedy

The highest-profile fan of J. Crew was Mrs. Obama.

She wore J. Crew many times during her tenure as First Lady, including an appearance on The Tonight Show in 2008.

According to a New York University study, traffic to J. Crew's website doubled after the 2008 TV appearance.

J. Crew fans were often seen wearing the brand's sweaters, outerwear, and heels. Gwyneth Paltrow, Jessica Alba, and other celebrities were seen in J. Crew.

Exterior view of J. Crew store with mannequins in window
A J. Crew storefront in 2011.
Paul Sakuma/AP

In 2010 it was announced that J. Crew would be taken private by two private equity firms, one of which had previously invested in the brand in the 1990s.

After the deal went through, Drexler got $200 million in cash and 8.8% of the new company.

The recession made shoppers hesitant to spend on items like apparel, so the deal came at a difficult time for retailers. The sale would give J. Crew time to adjust, according to Brian Sozzi.

He said that it will allow them to expand more aggressively, take a more pragmatic approach to opening more stores in the US, and possibly give them the balance sheet to expand internationally.

Row of models wearing J. Crew stand on stage at New York Fashion Week
Models present creations from the J. Crew Fall 2014 collection during New York Fashion Week.
Eric Thayer/Reuters

There were signs that J. Crew had high end ambitions. The J. Crew Collection was launched back in 2008 and has prices that are similar to luxury brands. J. Crew was at New York Fashion Week.

Drexler admitted that prices had gone up across the board and that J. Crew's offerings had become over-styled.

Sales dropped 3% during the holiday season as J. Crew's performance deteriorated.

"It has been a tough year for us, and the numbers speak to that," Drexler said during an earnings call.

J. Crew store
A J. Crew store in New York City.
Bryan Thomas/Getty

The company had a rough quarter. Professional women were the brand's strongest customers and had been hurt by the changes to the product assortment and manufacturing process.

There were a lot of issues to contend with. The brand had made mistakes with its inventory planning. Drexler said at the time that it hadmeddled with classic styles.

Many shoppers were turned off from paying full price due to the frequent discounts. Some shoppers who had been loyalists for decades were starting to grow tired of Lyons' edgier, high- fashion aesthetic.

One customer told The Wall Street Journal that it's hard for every person to find themselves in the J. Crew world anymore.

J.Crew AP Photo/Gene J. Puskar

The company said that it had reached an agreement with its lenders.

$400 million in funding from its lenders has been secured by the company.

"This agreement with our lenders is a critical milestone in the 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," Singer said.

During this process, we will continue to provide our customers with the exceptional merchandise and service they expect from us, and we will continue all day-to-day operations. As we look to reopen our stores as quickly and safely as possible, this comprehensive financial restructuring should allow us to thrive for many years to come.

Brandon Babenzien spent 14 years at streetwear brand Supreme.
Christian Vierig/Getty Images

Babenzien was the design director at Supreme for 14 years before launching Noah, which caters to older clientele. His designs for J. Crew hit stores in July and included bleached jeans, a pink plaid jacket, and "giant fit chinos."

According to Vogue, a Victoria's Secret veteran has overseen womenswear design for the past two years and has developed a devoted online following for her "effortless, nonchalant approach to dressing"

The men's and women's offerings have been well received. The men's collection was well received by both the men's fashion press and the customers, according to InStyle.

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