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Is Boston really the worst-dressed city in America?

Devoted to khakis, fleece, and comfortable shoes for generations, our style evolution is really (really) slow.

Illustration by Rudy Farber

Five years ago, GQ ranked Boston as the worst-dressed city in America, headlining a list that included Omaha, St. Paul, and Buffalo, all of which the magazine found notably, embarrassingly, more chic. “America’s Bad-Taste Storm Sewer” is how the writer described Boston, where “all the worst fashion ideas from across the country flow . . . stagnate, and putrefy.” Examples included boat shoes with socks, sportswear as formalwear, and khakis with pleats. Pleats! The accompanying photo showed a bunch of postgrad frat boys, a few of whom I’m pretty sure I went to college with, in pullover fleece and dad jeans.

It was not the first time this city has made such a list and it likely won’t be the last. On the one hand, it’s hard to rebut — a walk down any Boston street on any given day will showcase every one of these offenses. On the other, that same street might also produce a woman in a cat-print silk blouse by Stella McCartney or the $1,095 Rag & Bone lace-up leather pants that were so popular at the Intermix boutique on Newbury Street last fall that store leader Tina Markos had to reorder them twice.

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Still, it’s the khakis and fleece that people remember. Our reputation for being badly dressed is unshakable, and given our unironic devotion to the teachings of 1980s The Official Preppy Handbook(which, it should be noted, most of the rest of the world saw as satire), we’ve probably earned it. Somehow, though, we’ve managed to turn our tastelessness into a point of pride: How we dress, like how we drive, is a decision, not a deficit. Some like to say we’re too intellectual for fashion. That we have better things to spend our money on (like obscenely expensive housing). That it’s cold outside, and we’re practical people. And that, well, Uggs are pretty damn cozy. It’s not that we can’t dress better; it’s that we don’t even deign to try. “We’re not fashion victims,” Newbury Street retailer Alan Bilzerian told the Globe after the GQ takedown. “We’re confident enough to dress for ourselves.”

So we’ve only got ourselves to blame. Right?

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Maybe. But what if, instead, we’re the victims? What if we’re the product of retailers that buy into the cliche — and stock their stores accordingly, leaving us no choice but to perpetuate the cycle? As Newbury Street becomes ever more driven by chain stores with corporate headquarters in other cities and our reputation shows no signs of improving, it’s easy to wonder: Are we really a bad-taste storm sewer — and, if so, by choice? Or are we just buying what retailers have brought here to sell?

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Before I moved to Boston from New York in the mid-2000s, I went around to all my favorite stores and shopped as if I would never shop again. I had envisioned the Boston I’d visited in my ’90s youth — where the stores along Newbury were filled with Kelly green cable-knit sweaters and A-line skirts printed with fruits or palm trees. When I arrived, though, what I found was much different. Local boutiques like Stil, Stel’s, and, of course, Louis Boston were selling fashion-forward lines from around the world, dealing most especially in indie designers — names like Marni, the Row, and Loeffler Randall. They sold silhouettes no one else was carrying, and the vibe and color palette were most definitely more chic than cute. Louis owner Debi Greenberg was so influential that she could often demand citywide exclusivity for the lines she decided to carry.

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All three boutiques are gone. The Stel’s space is a tobacco shop; Louis Boston became a Restoration Hardware. Stil owner Betty Riaz now runs a yoga studio in Dedham’s Legacy Place.

In fact, very few independent retailers remain on Newbury, with rising rents having made keeping shop there untenable for nearly everyone but multinational chains: Zara, Anthropologie, and H&M on the “affordable” end and Valentino, Chanel, and Dolce & Gabbana on the upscale one. There are a few notable exceptions, including Alan Bilzerian, which has been in the same location since 1979, and its neighbor Riccardi, which opened in 1978. But many independent shops, their numbers dwindling in general, have been forced out to the South End, Beacon Hill, and beyond.

“When I first opened Stil 12 years ago, fashion tastes were superconservative,” says Riaz. “I think that stems from a deep-rooted culture in being more proper and from being one of the oldest cities in America. But I had plenty of fashion-forward customers. It was just a bit like a restaurant opening in a newly gentrified area, but getting there a bit too soon.” In many instances, once the novelty wore off, people returned to their comfort zones. And, well, the rent was exorbitant. “I always like to wish there might be a time when the independent stores might get more consideration on rent or some sort of break, because they’re needed and wanted, but as it is now, landlords are going to go for the people who can pay more,” Riaz says. “You sort of need to have independent funding to run an independent shop.”

Martha Pickett and Jane Schlueter’s shop dress opened on Newbury in 2005, closed in 2012, and eventually reopened on Beacon Hill, where Pickett says they’ve uncovered a generally more supportive community of businesses and residents. She insists that Boston shoppers aren’t as conservative as their reputation, “though, as a whole, we aren’t at the forefront of fashion here, either. I think we lean toward classic and understated more than anything else.” At dress, that means stylish, unfussy day and weekend wear: silk dresses, lace tops, statement sweat shirts, and lots of denim over $200. Now and again, she and Schlueter will take calculated buying risks. If it’s something they love but can’t quite picture who might buy it — like the $1,400 patchwork fur cropped vest by Sea New York — they’ll order only a handful. Even though those vests arrived in the store during an oppressively hot stretch in June, they ended up selling three within the first few days.

Positive response will, of course, embolden a store like dress to continue to push the envelope and bring in pieces that, while perhaps not quite avant-garde, toe the line between comfortably familiar and different from the same-old. Pickett says she and Schlueter recently started carrying a small selection from designer Rachel Comey, known for inventive pieces often inspired by the New York arts scene, that “flew out the door.” So there’s even more on the way next season.

As Betty Riaz says: “It’s kind of like when you teach a yoga class and you don’t know the students. You’re not going to throw in all the hard postures. You want to satisfy the interested beginners but provide what the advanced students need.”

But as Riaz sees it, while large chains can afford to take more risks, most don’t. When Neiman Marcus opened in the Natick Collection in 2007, where Riaz had a suburban outpost of Stil, she thought Boston had finally earned a shot at proving itself worthy of more interesting options. “But almost everything they brought in was conservative,” she says. (And less than five years after adding the luxury wing that Neiman Marcus anchored, the Natick Collection reverted to its considerably more pedestrian name — the Natick Mall. Walking from the “regular” mall to the high-end section, it’s hard not to notice the crowds get thinner and thinner before disappearing entirely.)

In part, the resistance to pushing the envelope is a product of corporate structure. While most big stores have a process in which out-of-town buyers communicate with floor staff who have daily interaction with customers, it’s still a process. In contrast, when owners of independent shops work the floor, the constant face-to-face contact allows them to tailor their buy to clients’ — and often even a specific client’s — tastes. “We analyze every customer, every purchase,” says Sari Brown, who owns and does all the buying for LuxCouture in Newton Highlands. She describes her customers as “professional women in their 40s to 80s; doctors and lawyers; women who sit on boards and have multiple homes, travel often, and spend their own money.” They have a comfort zone that Brown does her best to respect. “You can only push a little bit,” she says. “Extreme won’t work.”

Three years ago, Brown brought in a line of flare-cut cropped jeans. Nobody wanted them. “They said, ‘I can’t wear it; it’s so ugly,’ ” she recalls. “Fast forward, and Frame denim puts out a flare-cut cropped jean. We can’t keep it in stock. It’s a crystal ball thing. No matter how hard you try, you can’t rush them. When it clicks, it clicks.” And not a moment before. “We buy ‘safe with a twist,’ ” she says. “People make very few fashion faux pas shopping in my store.” Which is precisely why they shop in her store.

Harley Bilzerian, the women’s buyer at her father’s boutique, says that although she feels her clients’ tastes have progressed over the last few years, Bostonians’ readiness to embrace trends is slower than in other major cities. “It takes longer for them to catch on, but once they do, they get really into it,” she says. “They have to see it on other people first. Sometimes seeing it in a magazine helps them understand it better. A few of our clients look at runway shows online. Many see it on social media. But you still need to walk them through it.” Mixed prints, she says, are a work in progress. Color is only just catching on. “We had a woman in the other day trying on a dress,” Bilzerian says. “She says: ‘Well, it’s yellow. How am I gonna wear this again?’ ” She left without it.

Which would seem to confirm that the problem is with us. And, yet, Bilzerian says her most exciting buy this past season, Haider Ackermann — known for memorable pieces in animal prints and bold colors — has been a runaway hit. Among the best sellers: crushed velvet blazers and pants that are red velvet in the front and leather in the back. “I was like, this is a big wow factor,” she says. “I wasn’t sure who would love it.” Now, she says, “everybody’s fighting over it.”

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Illustration by Rudy Farber

While buyers for department stores and chain boutiques might not know the customer quite so intimately as the independent shops — at least not on the sort of first-name basis Sari Brown and Harley Bilzerian enjoy — it’s not like we get the leftovers from other cities. At most stores, an often complex buying process includes analyzing sales patterns and constant conversations with the stylists and floor staff who interact with the customers day to day. At the national chain Intermix, which has locations on Newbury Street and at The Street in Chestnut Hill, corporate analysts review each store’s performance at the end of every week, tracking sales and monitoring demand in addition to fielding reports from store leaders. If a piece, a line, or a category of clothing is underperforming in any given store, they’ll transfer it to a location where the market for it has proved bigger; as much as 30 percent of the assortment at any given time is what company president Jyothi Rao calls “responsive.” Similarly, if a store is getting a lot of requests for a piece that clients see online but which isn’t carried in that store, the system is set up to let buyers take those requests into consideration for the next time around.

Individual locations will also merchandise differently based on their clientele. At Intermix, a store window on Newbury might feature a leather jacket with a plaid skirt and Chloe studded booties, while the Chestnut Hill shop might put that jacket with a pair of jeans. “We work hard to understand each of our boutiques intimately and individually,” Rao says. “In Boston, we probably have fewer of the clients who want the super-edgy styles, but there’s a very fashionable clientele here. We’re not afraid to be sexy, but we might go for less color and print and pattern than in some of the other markets. But if we believe in velvet or ‘having a ’90s moment,’ we’re going to do that across the boutiques. In Boston, it just might not be as overt.” Rao says that the Newbury boutique has become one of the top performing locations among its 43 stores nationwide. “We use words like ‘elevated’ and ‘refined’ and ‘polished,’ ” she says.

And, contrary to our reputation as cheapskates, we do pony up. In addition to an assortment of new independent neighborhood boutiques, like the Back Bay’s ultra avant-garde All Too Human, and, farther out, Ava Boutique in Wellesley and Nine Streets in Newburyport, there’s been an influx of ultra high-end designer outposts, including Dolce & Gabbana and Valentino, plus recent expansions at Chanel and Hermes. After Louis shuttered its Fan Pier location in the summer of 2015, Saks Fifth Avenue in the Pru scooped up many of the more forward-thinking labels that became available, such as Marni and Dries Van Noten. Saks fashion stylist Suhail Kwatra is one of the “top producers” across the entire company, which means he sells more than most colleagues even in cities considered more fashionable. It’s a job predicated on relationships, but also, obviously, clothes that women like buying, and wearing.

“I do find that department store buyers have become more thoughtful and are paying more attention,” says Anne Lower, co-owner of Boston-based GordonLower Public Relations and one of Kwatra’s clients. “When I shop the Saks in Boston versus the Saks in Atlanta, where I grew up, it’s two very different product mixes. But it’s not as if Boston is getting all crew-neck sweaters and Atlanta is getting ball gowns.” In car-centric Atlanta, she points out, the shoe department is “an acre of shoes. You see things you never see here, but do you want to see them? Probably not. In Atlanta, there’s a market for seven-inch studded Christian Louboutins. Here, I walk around a lot on foot.”

At the same time, despite the influx of foreign wealth that’s transformed the city skyline in recent years, the international population — which has always been here, in some form — doesn’t seem to be transforming the fashion look of the city, despite having the cash to make a go of it. Even the most fashionable among us dress for the environment they’re in. Context matters. Or, as Betty Riaz puts it, “When in Rome, you know?”

Kerry Epstein, a personal shopper and stylist in Weston who has clients who will put down $20,000 at a time, says that customers have gotten more progressive since she launched her business 10 years ago. “Bostonians have become more sophisticated and more interesting in how they dress,” she says, “and I think the stores have both met that and are helping to move that along.” That said, most women she sees don’t come looking for high fashion. They’re moms who work full time and want an upgrade but don’t quite have the time to figure it out on their own. “They’re not sitting around perusing fashion magazines,” she says as she admires a $5,500 fur-lined parka by Mr. and Mrs. Italy at Barneys New York in Copley Place. “I mean, I could not get a client to buy this, but I’m so glad it’s here.”

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A note to GQ: There is a difference between bad taste, or disinterest, and pragmatism. Bostonians aren’t afraid to spend, though they’re likely to spend more on things they can wear often and keep for a while. “I take really good care of my clothes,” washing everything on the gentle cycle, rarely using the dryer, and dry cleaning as little as possible, says Anne Lower, who follows a motto of “buy less, but buy great.”

At French + Italian, which has locations in Beacon Hill and Marblehead, owner and buyer Aimee Lombardi says she and her customers talk constantly about cost per wear. “The New Englander is always going to want a utility to what they’re buying,” she says. “They want to get mileage. My customers love coming in and saying, ‘Aimee, I just wore this dress I bought from you six years ago.’”

It’s a philosophy that’s catching on. Witness the return of L.L. Bean’s Bean boot, long a Boston staple, now so coveted by the rest of the world that the waiting list for a pair has been as long as 50,000. There’s also the rise of “normcore,” a fashion movement described as an “embrace of bland, suburban anti-fashion attire” that took hold in Brooklyn and other young urban enclaves a few years back but which, arguably, Bostonians have been perfecting for decades.

Lombardi’s clients, for the most part, gravitate toward knitwear, coats, and dresses with staying power that can range from a few hundred to more than $1,000 per piece. “There’s a great quote I saw in Paris a few weeks ago: ‘Good style should show no sign of effort,’ ” she says. “I try to be thoughtful toward someone’s lifestyle. I’m not trying to sell you a leather dress that you won’t wear. I sell the cardigan you put on every morning or the shearling-lined clogs that take the sting out of going to the supermarket.” Footwear, she says, has to be practical. Comfort is big. That doesn’t mean she’s against a little gentle pushing. “We have a lot of one-shoulder tops, and we’re selling them,” she says. “But getting the customer to try them on is not always easy.” (Meanwhile, Sari Brown of LuxCouture says of the cold-shoulder look: “Wouldn’t touch it with a ten-foot pole.”)

And so, no, Bostonians won’t just buy something because it’s there, or because that’s all there is. If we can’t find something we feel comfortable in and feel good about spending our money on, we’re just as happy — if oftentimes a little too happy — to plumb the depths of our closet. More and more, though, we’re willing to take a chance, if given the opportunity.

Harley Bilzerian, for one, is particularly excited for her spring buy, which will include Lurex and sparkle, laminate, and, believe it or not, pleats. “Pleats!” she says. “They really don’t work on a lot of people. I bought a ton.”  

Alyssa Giacobbe is a frequent contributor to the Globe Magazine. Send comments to magazine@globe.com. Follow us on Twitter at @BostonGlobeMag.
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