The Best Fashion (and Food) Spots in Chicago
- Ken Downs
- Aug 14
- 6 min read
Fashion FYI’s in the Chi.
Chicago sits as the third-largest city in the USA, making it one of the many nationwide fashion capitals outside of NYC. Chicago fashion is unique — not as cutting edge and “trend-setty” as New York, nor as basic and athleisure-driven as L.A. Any Chicagoan will correct you if you dare call it a Midwestern city. The city transcends Midwesternism, distancing itself from its own Lululemon and PacSun suburbs, and instead prides itself on its working-class culture via (vintage) Carhartt and Dickies.
If you’re looking for fashion in Chicago, you should explore three neighborhoods: the Gold Coast, the West Loop, and the infamous Wicker Park.
GOLD COAST
The Gold Coast (as you can tell from the name!) is home to the city’s millionaires, billionaires, and dozens of luxury shops for them to peruse. At the north end of the infamous Magnificent Mile, you can escape gawking tourists and chaotic traffic and seek a peaceful refuge at The RealReal, get lost in Aritzia, or window shop for Lamborghinis. From Chicago Avenue, you can zigzag your way, smelling the exuberant amounts of wealth this neighborhood has to offer.
WHERE TO SHOP
TheRealReal specializes in preloved luxury. Having recently downsized, the vibe has become very relaxed and intimate. TheRealReal embraces a wide variety of styles in its well-curated sections. Their sections include Modern Luxe, Street Maven, and the ever-so-classy British Countryside. They also actively buy luxury items!
The Loewe store is a brand-new addition to Chicago’s booming luxury scene. As soon as you walk in, you’ll be greeted with the most beautiful collection of buttery leather bags. Also, HUGE shoutout to Lo, who gave me a tour and showed me her faves (including their new Campo denim boat shoes that are now on my wish list!). The boutique is on Oak Street, a street lined with many more high-end retailers covering a variety of styles from BAPE to Hermes.
Kith is a streetwear lover’s dream. Coming soon to the neighborhood, Kith will open its first doors in the Midwest to join its other locations throughout NYC, L.A., and Miami. Housing the coveted Coperni and crisp Casablanca, Kith is set to make a mark in Chicago’s fashion sphere.
WHERE TO EAT
3 Arts Club & Café ($$) is if IKEA was reinvented by RHONY’s Brynn Whitfield. Have a delicious brunch at their opulent restaurant and then explore the six floors of interior decor inspo 3 Arts has to offer.
If you’re particular about how you like your steak, go to Gibson’s ($$$). This Chicago staple will give you a luxurious dining experience that will truly make you feel like money. If you have room for dessert, you can't skip their macadamia turtle pie that stands nearly as tall as the Hancock Tower. It’s a level of decadence you can’t find anywhere else in the city.
If you want some Chicago-style deep dish, head to Lou Malnati’s ($). Every Chicagoan will tell you it’s not true Chicago-style (it’s pizza cut in square slices), but we all recognize deep dish as a tourist trap. It’s worth a taste, but by Chicago Law, if you live in Chicago, you can never have it again.
WEST LOOP
The West Loop has changed a lot in the past 15 years. It’s gone from an old industrial district of warehouses to luxury lofts and corporate offices for the likes of McDonald’s and Google, while the bars, shops, and restaurants offer a playground for Gen Z and Millennials. Oh, I forgot to mention: Soho House Chicago is tucked right off Randolph Street.
WHERE TO SHOP
Between Randolph Street and Fulton Market, locals dine, drink, and shop their hearts out. Aside from chain faves like Free People and a flagship Patagonia store, every local streetwear enthusiast knows about Notre and SVRN. West Loop is also home to several bars and world-class restaurants such as Au Cheval and Bisous, establishing West Loop as Chicago’s favorite social playground.
Notre houses brands such as Acne, Entire Studios, and Ganni. The store’s vibe is cozy and free, with an open lobby perfect for exclusive in-house events and spaces allowing you to immerse yourself throughout the store. In the back, you can find a room of freshly curated vintage finds, including classic Levi 501s and varsity gear from the ‘70s.
SVRN is a boutique with phenomenal editorial direction from its site alone. The store gives the ultimate boutique experience, complemented by the smooth aromas of Margiela Replica fragrances. If you like a Rick Owens kind of vibe, this is the place for you. SVRN has proven itself to be on the pulse of fashion, catering to a customer with an edge. If you love a classic style with a bit of edge, they carry Dries Van Noten. If you like more edge, they have Willy Chavarria, too!
WHERE TO EAT
The Drip Collective ($) has an amazing feel. It’s a super casual coffee shop with great music, and it even hosts networking events sometimes! Often airing anime or old movies on their projector, Drip Collective establishes a cozy feel for Chicago’s most eclectic and fashionable. Their Turon drink (made with banana milk) is something I didn’t know I needed until I had it.
Au Cheval ($$) isn’t your average burger joint. This spot is great for after-work drinks, a date night, birthday dinners, or whatever! With a rustic feel and a homey vibe, Au Cheval won’t disappoint for a night on the town. Whatever you get, go ahead and ask for bacon. You’re welcome.
Trivoli Tavern ($$$) is perfect for anyone who wants a moody yet whimsical ambiance. Hidden away in an alley, Trivoli will transport you to 1920s Chicago. The menu has something for everyone, from savory pasta to fresh sushi selections. The drinks are amazing (my personal fave is the Bella Punch). If you’re ever in Chicago during the three months of spring/summer we have, def get a table in the alley.
WICKER PARK
Wicker Park is essentially Chicago’s answer to Williamsburg (take that as you will). The Milwaukee-Division-Damen triangle and surrounding area are home to Chicago’s premier indie boutiques and vintage shopping. Vintage pop-ups, such as curations a la Olio, are scattered up and down Milwaukee Avenue. If you crave a sneaker, hit up Saint Alfred. They have your Asics, New Balances, and Salomons. If you have a wicked taste and want a unique boot, visit John Fluevog. And you’re bound to find stellar second-hand streetwear finds at Round Two. You also can’t miss the dimly lit dives in the area. (If you can make it to the bathroom without getting sidetracked by a beer-boozed patron at Gold Star or Rainbo, you’re not doing it right.)
WHERE TO SHOP
Away from the Milwaukee Ave. bustle, you can find a more curated experience. On Division, there are three boutiques that neighborhood locals and tourists love: Gemini, Independence, and Penelope’s.
Independence is for denim lovers. If you like a classic all-American flare with a twist, this is the place. They also carry Japanese denim and one-of-a-kind designs that you can’t find or compare anywhere else in the city.
Gemini and Penelope’s are sister stores for those who value fun, freshness, and sustainability. Penelope’s is for that playful young adult finding their way through fashion, experimenting, but on the right track. Gemini is for that same person who has found their unique sense of style and owns it through and through. They express themselves through their Wax London cardigans and Paloma Wool skirts, always leaving room for wardrobe development.
WHERE TO EAT
After a fun day of vintage shopping in Wicker, you’re bound to develop an appetite. If you’re craving a cheap, greasy burger and fries, then Devil Dawgs has your order. If you want to enjoy some of the best French dining in the Midwest, Le Bouchon is right at Six Corners (the busiest and most daunting 6-way intersection in the city). The Chicago food scene is indubitably one of the most diverse food scenes in the country, and the options available in Wicker Park are just colorful examples of that.
Phodega ($$) is pho-nomenal. Just across the street from Penelope’s, Phodega has some of the best pho in the city. Their portions are big, so it's lunch and dinner served. The restaurant also carries some Vietnamese drinks and snacks right by the counter (which are also cheaper than regular snacks at a convenience store). If you’re not in a pho mood, their fried chicken fried rice is delicious — even more so with their sauces mixed in. It’s broiled perfection.
Bongo Room ($$) is an absolute brunch go-to, especially for people with a sweet tooth. The pear and apple challah French toast is scrumptious and will guarantee to fill you up and power you for a day of shopping.
Established a block away from the Shit Fountain (real thing), Kasama ($$) has earned itself the reputation of being the premiere restaurant on the near west side. Kasama specializes in putting zesty twists on Filipino cuisine. Having gone viral on TikTok for their now-infamous longanisa breakfast sandwich, it’s no wonder there are 2-hour waits on any given morning to get in (you can’t make breakfast reservations either). 🌀
Ken Downs is a writer, fashion stylist, and certified hater who, in high school, was nominated as Most Likely to Be on Reality TV. He is a fashion writer for HALOSCOPE. You can follow him here on Instagram and TikTok.
