J. Crew has had a rough couple of years. Chairman Mickey Drexler and Creative Director Jenna Lyons, once the dynamic duo of accessible fashion, have buckled under the weight of a changing retail landscape. 

Jenna Lyons, Executive Creative Director and President of J. Crew, took the helm in 2011, when revenue pushed $2 billion, and the brand was seeing unrivaled success in the retail sphere. Just two years before, Michelle Obama and her daughters wore J. Crew dresses at the Presidential Inauguration, and the retailer was poised to take its place at the top of the hierarchy of American retail. 

Over the last six years, however, J. Crew’s loyal fans have seen the store move in a trend-setting but unfamiliar direction. Gone were the preppy days of the cardigan and the tweed pencil skirt, and in came camo cargos, fur vests, and the rest of the stereotypical hipster wardrobe. Loyalists left in droves due to size discrepancies and a departure from the classic brand they had come to love. 

In 2018, J. Crew will be forced to repay $2 billion in outstanding debt. The retailer posted a loss of over $670 million in the 2014 fiscal year. Retail insiders knew something had to change, but the departure of Lyons sent shockwaves through the fashion community. 

The problem is that J. Crew attempted to punch outside its weight class. Lyons steered the company in a direction that brought it closer to a fashion house than an actual mass-marketed retailer. It’s never a good idea to walk away from your core customer, and J. Crew did just that. Lyons wanted J. Crew to set trends instead of follow them, and the company suffered for it.

With the rise of online shopping and fast-fashion such as Zara and H&M, classic retailers have to make changes to try to compete in a changing arena. The shakeup at J. Crew reminds us that fashion is a risky business, and even iconic brands aren’t insulated from an evolving retail landscape.