The 10 Worst-Dressed Cities In America

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Photo: johnrobertshepherd/Flickr

When it comes to dress sense, what’s worse: layer upon bulky layer of long underwear and puffy coats? Flashy, barely-there outfits? Or downright sloppiness?Travel + Leisure readers rated major destinations in categories including style for the annual America’s favourite Cities survey—and the results confirm that city dwellers fall short of fashionable in myriad ways. But it’s Anchorage that earned the dubious honour of No. 1 worst-dressed city in America.

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That’s no surprise to Dr. Miriam Jones, a paleoclimatologist who has traveled in and out of Anchorage “too many times to count” during a two-year research stint. “It’s not uncommon to see oversized parkas with fur-lined hoods and bunny boots, and people aren’t alarmed when a person wearing a ski mask enters a room.” In Alaska, she adds, men sport beards and flannel in the most un-ironic way possible: to keep frostbite at bay and their appendages attached.

Baltimore, on the other hand, can’t blame icy temperatures for its #3 place on the worst-dressed-people list. According to eight-year resident Erika Poniske, locals dress poorly for a host of reasons, some of which can be attributed to city subcultures. Baltimore hipsters, she says, bypass the tried-and-true thrift store, opting to dumpster dive for their clothing instead. And if you spend enough time in the quirky neighbourhood of Hampden, you might just run into a woman wearing her hair in a real-deal ’50s beehive.

Poniske believes it’s the city’s die-hard commitment to all things casual that makes it most deserving of its ranking. “If you’re going to take time to dress up in Baltimore, you better be on your way to somewhere specific. Otherwise you’re going to stand out, and you’re going to feel awkward.”

But a reputation for luxurious tastes doesn’t necessarily translate into smartly clad residents either. Take Dallas, which T+L readers consider a top 10 destination if you’re into upscale shopping, but which came in as the No. 6 least-stylish city.  

Dressing well certainly has an element of personal taste, and this survey is based on visitors’ perceptions, not scientific fact. So, did T+L readers deem your city to be one of America’s worst dressed? Read on to find out, and feel free to defend local fashions in the comments.

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#10 Kansas City, MO

America's #1 city for barbecue does not a fashionista make.

Kansas City residents are among some of our nation's friendliest, and they can school anyone and everyone about the intricacies of grilling, but it looks like they're lost when it comes to putting together an outfit.

#9 Phoenix/Scottsdale

Here's a hint: if a city has a museum exhibit dedicated to the bolo tie, it's not going to be fashion forward. The official neckwear of Arizona (yes, that's a thing) is enjoying a comeback.

But sunny Phoenix made the top 10 for spring break destinations--when attire is almost beside the point.

#8 Portland, ME

With some of the most limited shopping options in America and one of its least diverse populations, Portland is not where you come to try on cutting-edge clothing.

But that's just fine, because the city slays the competition in other areas, placing first in five survey categories, including best summer destination and best drivers.

#7 Atlanta

If the flashy reality-TV stars of The Real Housewives of Atlanta are at all indicative of how the rest of Atlanta dresses, it's no wonder our readers ranked it as America's #7 least-stylish city.

Hotlanta has one of the highest per capita incomes of any southern city, but as the TV show illustrates and the saying goes: money can't buy taste.

#6 Dallas/Fort Worth

#5 San Antonio, TX

San Antonio is known for rodeos, not runways.

Take the famous San Antonio Stock Show & Rodeo, a three-week extravaganza at which you won't feel comfortable unless you're suited up in western attire--from your head (one of those sweet hats) to your toes (cowboy boots).

#4 Orlando

Orlando was voted the No. 1 family vacation destination, so visitors were likely focused on people seen around the theme parks, which aren't exactly crowded with fashionistas--enduring Disney World's winding lines in stilettos would be crazy.

The city won raves for its weather and variety of hotel options.

#3 Baltimore

In a city judged to have fairly offbeat residents, there are bound to be questionable fashion choices. Case in point: the Baltimore Hons, a group of people who sport the '50s cat-eye-glasses look with gusto.

Some visitors have their sights focused elsewhere, anyway, using Baltimore as a convenient, affordable base for day trips (ranked #12).

#2 Salt Lake City

Voters rated Salt Lake City one of the top 10 quietest cities in the nation and praised it for affordability and cleanliness.

But T+L readers didn't equate those squeaky-clean locals with fashion-forward ways--perhaps because, male or female, there are only so many ways to rock a polo shirt.

#1 Anchorage

In chilly Anchorage, the dress code leans toward practicality rather than fashion, and many residents teeter through the streets bundled as tightly as Randy, the kid brother in A Christmas Story.

Fashion trends take longer to reach this hinterland, but travellers are happy to make the trek regardless--especially in summer--and rated the city #4 for peace and quiet.

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