A recent Saturday Night Live sketch featured a parody store called Fashion Coward, “the only store for people who hate shopping and feel lost and scared.” Contrasting its neutral cardigans with the edgy jackets worn by the truly fashionable, the fake commercial proudly announced that “we keep it safe with things like ‘brown sweater’ and ‘pants for the legs.’” At one point, the actor Emma Stone, playing a customer, says that if fashion tells a story, Fashion Coward’s is, “I’m a stranger to myself.” The end of the skit reveals Fashion Coward’s inspiration: Ann Taylor.
Ann Taylor, the tried-and-true, white-collar women’s retailer, is in the strange position of being both ubiquitous and ubiquitously mocked. Most women whose titles end in something like coordinator or manager likely own a pair or two of Ann’s sexy-but-not-too-sexy slacks. In Washington, D.C., where I live, it’s as though women are issued a pencil skirt and ponte top, Gilead-style, upon signing their lease. I regularly see women wearing the exact same outfit on the metro.
And yet, to admit to shopping at Ann Taylor or its slightly cooler cousin, Loft, is to admit fashion defeat. Ann Taylor is “where aspiration meets motivation meets resignation, and that is why it is perfect for Washington,” the columnist Monica Hesse once wrote in The Washington Post. In the world of mall retailers, it’s in a slightly awkward clothing category between dirt-cheap Uniqlo and the kind of striking outfit you’d want to wear to a dream-job interview. As the retail reporter Mallory Schlossberg wrote in Business Insider, Ann Taylor is “not as cheap as a Forever 21 or H&M. It’s not sexy and sharp like Zara. It’s not for preppy fashionistas (with money to burn) like J. Crew.” Indeed, Ann Taylor’s parent company, at the end of 2017, admitted to having made “fashion missteps.”