A Gentleman's Guide to Looking Good in Chicago

Beards are always in season in Chicago.
Beards are always in season in Chicago. | © Beardoholic.com / Flickr
Photo of Sarah Ashley
16 May 2018

A quick Google search of “Chicago fashion” could very well result in a long list of North Face coats and Patagonia long underwear. However, Chicagoans accept the intense winter (and summer) weather as a challenge to look classy in spite of extreme temperatures. In fact, embracing this fickle climate has yielded some fashion trends even New York and LA can agree are on point.

Facial hair

Beards are huge in Chicago – meaning both large and en vogue. They keep men’s faces warm when it’s cold and, though it seemed their heyday as hot trends in hipster neighborhoods had fizzled out, beards are popping up more and more around the city. The key to having a good-looking beard is maintenance. Gentlemen do not have scraggly beards; gentlemen have groomed, healthy facial hair. Trim those split ends and use a beard oil to keep your beard sleek and smooth. Places such as Pete’s Barber Shop in West Lakeview offer honest advice (sometimes insults) when it comes to hairstyles and beards. Pop in for a shave, haircut, or beard trim. Owner Pete Huels is no-nonsense and has a fridge full of beer next to an Xbox in the waiting room. Not a bad place to get groomed.

Beards are always in season in Chicago. | © Beardoholic.com / Flickr

Trench coats

The key to looking good consistently in Chicago is the jacket. Jackets, coats, and outer layers of all kinds must be stylish and functional. No sense in looking cool if you’re unprotected from the elements. According to Jason Pullan of The Chicago Chic, trench coats are perfect for those strange weeks between spring and summer when it could be 80° F (26.7° C) and sunny one minute, then start to thunderstorm the next. Trench coats are also excellent for complementing business casual attire and upgrading relaxed weekend outfits. Though Pullan wears a Banana Republic trench coat in khaki, try out a slightly more surprising color: navy. It adds a touch of sophistication – something all gentleman can get on board with.

A navy blue trench coat is a versatile and stylish option for spring, summer, and fall. | © FLATSEVEN / Flickr


According to GQ magazine, mens’ streetwear this year is all about windbreakers and tracksuits. This is terrific news for Chicagoans, as living in the Windy City does get super blustery. Gentlemen looking for a little guidance should start with a simple bomber jacket or a pair of track pants. Wearing an entire matching set, such as the original Adidas black and white striped tracksuit, is definitely a great look, but can be intimidating to try all at once. Bomber jackets at Zara achieve the same chic athletic style without overdoing it. Bonus points if you can find one that actually offers protection from the wind.

Bomber jackets pair well with jeans or matching track pants. | © vanes_hud / Flickr

Hot shades

The right sunglasses can take a summer getup from “Meh” to “Meow!” As summer kicks into high gear, Chicagoans everywhere shift from winter wardrobe to summer duds, and this often means much less thought goes into ensembles. This is totally understandable, but doesn’t have to mean forgoing style for comfort. Sultry shades like Ray Ban’s classic aviators or Warby Parker’s Fletchers instantly give gravitas to any relaxed summer look. Think of sunglasses like an investment into the cherry on top of the sundae: Without it, you’re just a pile of creamy beige.

A hot pair of sunglasses, like this Ray Ban set, is the perfect finishing touch to an ensemble. | © Rich Niewiroski Jr. / WikiCommons

Desert boots

If there’s a perfect shoe to take gentlemen from day to night, it’s the desert boot. According to Esquire, these boots are super breathable, which means they can be worn with socks or without. The shape is classic, with minimalist laces and a business casual vibe. Yes, Esquire has a pair from Clark’s on their list of summer shoes, but these are definitely worn year-round in Chicago. They pair well with thick scarves in autumn and trench coats (see above) in spring. Plus, desert boots work well at everything from a company outing to a BFF’s BBQ. Just like shades, shoes have a big impact on your look, so don’t skimp in either department.

Desert boots are quintessential Chicago footwear for men. | © ercwttmn / Flickr


Perhaps its Chicago’s past as a hotspot for gangsters and gambling that makes blazers on men such a fitting choice. Whether paired with a fedora or a tattoo sleeve, a solid blazer is the ultimate finishing touch to any gentleman’s outfit. No longer are blazers for the office only; linen blazers are great options for more casual settings, too. Zara offers tons of styles, from sleek black suit coats to loose, checkered patterned versions. Bonobos, which offers 20% off services for first-time users, features Italian wool and stretch fabric blazers, not to mention an enormous collection of shirts and suit pants chosen based on body type and measurements. No matter the style, a solid blazer can turn any dude into a Chicago gentleman.

Blazers work just as well with three piece suits as they do with jeans. | © Conor Clinch / WikiCommons

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