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.
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.
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.
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.
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.
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.
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Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.
Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.
Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.
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