Stylish Looks by the Neighborhood: Fashions that Embody Every Corner of the City

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Chicago is a city of neighborhoods and these small, distinct pockets have their own character, style, and culture.

Many of their inhabitants have more civic pride for their chosen neighborhood than they do for the city at large. This is the way we big city dwellers construct a feeling of neighborly intimacy within the anonymous metropolis. We’re all Chicagoans, but we’re also Lincoln Parkers, or Pilseners or Uptowners. And, often, our personal style matches these unique towns within a town.

Here, we take a look at the fashions that embody each neighborhood.

The Loop

barbour store

The pulsing heart of Chicago business is characterized by professional polish and efficiency. Many modern offices have gone business casual, with an emphasis on “casual,” but in the high-in-the-sky offices of The Loop, the business suit is still boss. There’s certainly a wide range of professional looks, but those that do it best excel with either custom-tailored classics or modern, slightly avant garde updates.

There are really only two ways to look bad in a suit — wear one that’s ill-fitting or terribly out of date. Even if you continue to fall back on traditional styles, you should invest in custom tailoring so that each piece fits you like a glove.

Ladies: To shake up the professional look, try different silhouettes. The jumpsuit, for example, has made a comeback, and many designers are making chic versions that are absolutely work-appropriate for the stylish, modern career woman.

Gents: Choose a slimmer fit, narrow lapels, a skinny tie and more colorful accents. If you really want to step out of the ordinary, hop on the patterned suit trend – you can go for a bold mix of patterns or stay more subtle with low-contrast plaids and solid accessories.

Gold Coast

gold coast style

Chicago’s Gold Coast is very aptly named as it has an unmistakable feel of wealth and class. This stately neighborhood is home to some of the most valuable real estate and exclusive shopping in the city and it’s been home to the city’s most influential VIPs: Potter Palmer, John Jacob Astor, and Hugh Hefner.

The name of the game in the Gold Coast is big name designers. The net worth of a given Gold Coast resident’s outfit is likely more than the average Chicagoan’s monthly rent. Style is all about luxury, high fashion and impeccable taste. You may even do double-takes at the Gold Coaster, thinking he or she may be famous…and you might be right.

Ladies & Gents: The luxuriously fashionable men and women of the Gold Coast like their designers and they don’t leave the house without looking perfect. Even errands or a trip to the gym finds these Chicago A-listers looking like they stepped out of Vogue. Head to the Oak Street shopping district for a jaw-dropping selection of designer boutiques. Even if you can’t spring for a designer outfit, you should grab lunch at an outdoor table and treat the sidewalk like a runway for a bit of style inspiration.

Logan Square

logan square style

The epicenter of the hipster continues to shift around west-side neighborhoods. A decade ago it was Wicker Park, but the rent prices and proliferation of Starbucks and sports bars long ago drove the hipster to less gentrified hoods like Logan Square and Humboldt Park. These areas, like Pilsen, are now shared by the longtime Hispanic residents and the hip crowd that seeks reasonable rents and corner dive bars.

The style here is quirky, vintage-inspired and bohemian. You have a good amount of freedom when it comes to pulling off hipster chic, but there are definitely a few staple trends: unusual eyewear, vests, leggings, skinny jeans, flannel, cowboy boots, and plaid. If you’re trying to get the look, just think of what you might wear for a day that included a few hours in a 70s university library as well as an outdoor music festival.

Ladies: Think layers, vintage, and rough-around-the-edges feminine. Many of the same things that made hippie girls cool make hipster girls cool too. It’s the easy, boho style that doesn’t appear to be trying too hard that works best.

Gents: Think lumberjack meets nerd meets hip musician and you’ll have a pretty good grasp on the male hipster look. It’s a great style for the lazily fashionable guy. Throw on a pair of skinny jeans, a plaid flannel, black, thick-rimmed glasses and a beanie and you’re all set for bicycling down the boulevards or enjoying a locally-sourced meal at Café Lula.

Lincoln Park

logan square style

This upscale northside enclave has long enjoyed the status as the yuppie capital of Chicago. The gorgeous red brick row houses, high end boutiques and lively nightlife make this hood equally appealing to locals and tourists.

Those who live and play in LP are generally of the wealthy, country club variety. The streets are populated by polished young moms pushing strollers full of kids with last names as first names, young professionals, and DePaul students. This mix lends itself to a classic preppy style which, luckily, doesn’t change too dramatically from year to year. It’s all about pastels, polos, and boat shoes.

Ladies: Go for well-tailored, clean and simple. You’ll fit right in with a pair of slim-fitting black capri pants, a linen blouse and a light cardigan thrown over the shoulders in case it gets chilly. Just don’t forget a pair of large sunglasses, and a designer handbag.

Gents: For a day in Lincoln Park, imagine that you’re heading to an upscale brunch and then spending the rest of the day on a yacht. You can’t go wrong with well-fitting, flat-front khakis, a polo or button-down and a classic pair of Wayfarer sunglasses.



Like many Chicago neighborhoods, Pilsen has dramatically changed over the last several years and continues to change every day. Now, there’s a unique dichotomy between the large Hispanic community and the edgy new transplants. Because of its nearness to UIC and its relatively cheap rent prices, Pilsen has become a haven for college students and young, artsy types alike.

The style in this neighborhood on the rise skews a bit punk and is heavy on leather, and military-inspired fabrics and colors. With the number of funky thrift stores and art galleries, fashion here is also what you make of it. Cobble together vintage and new, mix aesthetics and go for an unexpected look that expresses your inner artist.

Ladies: Channel the Pilsen vibe by pairing pieces that you might not normally put together. When it comes to edgy style, the only real rule is confidence. No matter what you wear, just make sure that you own it. The only clothes that will garner strange looks are buttoned-up, conservative ones that may make you look lost.

Gents: For male Pilsenites, denim is big. The coolest variety tends to be the super dark washes that have a slightly working man’s feel. This is definitely the area to wear your intentionally ripped-up jeans with paint splatter. Pair them with a quirky vintage t-shirt and a lived-in leather jacket and you’ll feel right at home.

What we love most about Chicago is that each neighborhood has a special flavor. Hopping from one neighborhood to another can sometimes feel like you’re traveling to multiple cities in one day.

Longtime Chicagoans have an intimate knowledge of the city’s diverse areas and choose to live in the one that feels most like an extension of who they are. But, occasionally it can be fun to travel a bit outside of your neighborhood’s borders to try on an entirely different style.

Maureen Lampert is the president of the Oak Street Council, an association of Chicago boutiques and businesses such as Barney’s, Furla, Hermès, Jimmy Choo, Kate Spade and many more. Maureen is also vice president of Lester Lampert, a custom jewelry store on Oak Street. For more information, visit Oak Street Chicago.

About UPchicago Team

Urban Philosophy is a way of thinking that you develop when you’re a true city person. Whether you’ve spent your whole life living in Manhattan, or you just moved from small-town Iowa to the city of Chicago, the longer you stay, the more you come to understand what it means to live in a city. Our Urban Philosophy is that no matter who you are, where you are from, and what your likes and dislikes may be, there’s something for everyone in city life.

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