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For teens in the early aughts, an afternoon at the mall was the pinnacle of socialization. Popping into Abercrombie, American Eagle, or the Gap with your best friends and stopping by the food court to nosh on an oversized pretzel after — ah, how we long for those simpler times.
Editorial consultant Lauren Caruso remembers how, growing up in suburban New Jersey, she’d go with her mom to the mall whenever she needed something, where one specific place stood out: “Ann Taylor was one of the first stores where she tried something on and came out of the dressing room to ask me what I thought.”
Though the years since have seen the devastation of malls as a physical space, the brands that dominated the fluorescent-lit caverns of capitalism have found a new footing online. First, Abercrombie came back into focus. Then, group chats were full of texts about the new Banana Republic. J.Crew quickly followed suit, under new creative director Olympia Gayot. Now, it’s Ann’s turn.
If you’ve walked past an Ann Taylor store — at the mall or otherwise — or come across its feeds, you might notice it looks… a little different. Once a bastion of women’s workwear, it’s re-entered the conversation, among friends and colleagues alike, despite shifts in what dressing for work actually looks like.
“Women want to be pulled together but still comfortable and fashionable wherever they may work,” says Heather Gruccio, the brand’s SVP Merchandising. “So many women are surprised when they see what we look like today.”
Caruso was recently one of those women. “It’s obvious that the brand is paying attention to what women want without completely abandoning its core customer,” she says. So much so, that she committed to becoming an official partner of Ann Taylor.
Taking a page out of the handbook of successful DTC brands like Reformation and Everlane, Ann Taylor is harnessing the power of influencers like Caruso to serve as a sort of online lookbook, re-introducing shoppers to the brand and the myriad of ways it can be worn. In new stores, digital monitors will feature this content, offering real-time ideas for customers pulling things into a dressing room. In addition to these creators, Ann Taylor has also been dressing celebrities like Katie Holmes, Viola Davis, and Drew Barrymore, who, while in their 40s and 50s, have enduring personal style that manages to toe the line between playful and sophisticated.
Ann Taylor’s shift began when it was acquired in 2020; now, it’s part of The Knitwell Group, which also includes Loft, Chico’s, and Talbott’s. Part of its recent success, though, has been the brand’s ability to lean into its original DNA, doubling down on workwear even as women log on from home or shift the way they dress for the office. It’s continued to embrace classic corporate silhouettes — trousers with matching blazers, slim-fit cardigans, button-down shirts — in high-quality materials, all while keeping the prices affordable. (Apparel ranges from $20 to $348, with most pieces available in sizes XXS-XXL and 00-22.)
“While there are many great smaller brands customers can discover and shop, there’s equity and trust built up over time of many of the ‘mall brands’ that women have grown to know and love,” Gruccio explains. “We have 70 years of heritage to work with. We know how to make incredible sportswear separates, but I also think you know an Ann print when you see a woman walking down the street in one.”
For those going through major moments in their professional lives — starting a new job, returning from maternity leave, or even just stepping back into the office after a minute — there’s a certain comfort in knowing exactly what you’re getting when you’re shopping at Ann Taylor. At the same time, with the growing popularity of tailored workwear, neutral hues, and a buttoned-up sophistication in the wake of the “quiet luxury” trend, there’s a certain flattening of the style curve, making it tough to differentiate between brands that all seem to be reaching towards the same greige blazers. Ann Taylor is breaking through that by offering those wardrobe essentials, but embracing its design roots in florals and flouncy details.
As perhaps you’d expect, the brand’s new arrivals page offers a mix of preppy separates, like a cropped polo ($85) or paisley jacket ($198) alongside classic workwear pieces like a plaid trouser ($139) or shift dress ($159). There are mini skirts and tanks, but, in general, Ann Taylor plays to a slightly older, more conservatively dressed audience. That doesn’t mean there isn’t something for Gen Z to tap into: A brand that’s trend-aware without being overtly trendy serves as a great place to pull together the building blocks of a more put-together wardrobe. In fact, it may be more of a generational phenomenon that shoppers discover when the time comes to invest in a work uniform of their own.
“When I started looking for my first big girl job in 2008, I couldn’t really afford much, so I went vintage shopping and found a vintage Ann Taylor blazer that I wore to the interview and my first day,” says Caruso. Now, a new era of corporate girlies are shopping — whether they find out about the brand through influencers, friends, or a parent.
The word cool often gets thrown around in the context of many modern brands — that to be successful, there has to be a certain je ne sais quoi that generates buzz and convinces people to get on board. Ann Taylor seems to have found a workaround: Chasing cool is an impossible task, but staying true to what women want with good quality, affordable pricing, and clothes that make them feel great when they put them on is enough to keep shoppers coming back, no chasing needed. That seems plenty cool to me.
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