Windy City Style: 7 Best Menswear Stores in Chicago

If you’re looking for cool menswear stores in Chicago, look no further. Read on to see the best menswear stores in The Windy City.

Chicago’s has a rich and unique sartorial history. Torrid summers and frigid winters make function equal to form, even to the most art-focused designers. 

The result is a community of Chicago men’s fashion stores with thoughtful approaches to design and curation, thanks to their Windy City roots.

There are plenty of upscale boutiques on Michigan Avenue, but the born-and-bred Chi-town shops are spread throughout the city’s neighborhoods. Fortunately, these unique local shops offer all sorts of stylish duds, from jeans to formalwear to elevated workwear.

The 7 Best Men’s Clothing Stores In Chicago

Here are eight menswear stores in Chicago, each with distinct offerings, in no particular order…

Independence

Launched in 2012, Independence is a craft-focused trove filled with hip American-made fashions and one-of-a-kind finds. After all, the shop was founded by George Vlagos, the son of a shoe cobbler.

Their high-end, in-house line of boots, Oak Street Bootmakers, is designed by Vlagos and 100% made in the USA, even down to the care products.

Oak Street builds all of the quintessentials, from comfortable summer moccasins to their Horween leather Lakeshore boot. This boot will wear in long before it wears out. 

A few of their 50 US-based brands include LVC Jeans, the ever-masculine American Optical sunglasses, and Gitman Bros -for those of you looking to acquire the perfect vintage-inspired two-pocket flannel. 

Independence has an excellent collection of genuine vintage too. Recent finds include a rare pair of medium-washed Levi’s and a lone turquoise concho pin. They’re even cataloged and tagged with individual lot numbers, like an art auction house does.

This is Chicago’s everyman fashion store. It’s a curation of timelessly cool pieces, appropriate for artists or bankers. It’s unpretentious but undeniably upscale because of its focus on craftsmanship.

The mix of tried-and-trues and the creatively-sourced make the store an easy place to find hip basics, and a fun place for the sartorially curious.

Cowboys and Astronauts

Upon stepping into this lifestyle boutique, you’re welcomed by a life-sized astronaut figure. This conveys the hint of irreverence you’ll find in the fun yet sophisticatedly curated collection at Cowboys and Astronauts.

Peruse their shirt racks for distinctly-detailed polos or short-sleeved button-ups in bright colors and eye-catching patterns. They stock a lot of lively and sustainable pieces from the notoriously eco-friendly Toad&Co brand.

If you’re looking for practical outerwear, you’ll find field blazers and chore coats from classic heritage lines like Barbour and United by Blue, which recently featured an effortlessly stylish puffer jacket on the store’s shelves.

Bonus points for their impressive mark-down section, created to make room for new rotations, not because the pieces are unappealing. Their affordable in-house basics, a collection of preshrunk t-shirts, feature hip Jenny Holzer-esque graphic letters.

Spirited statements like “We Are Midwest” make these t-shirts must-haves, especially for proud Chicagoans no longer in Chicago (like a college alumni shirt). They also sell the same shirts with the stylish Cowboys and Astronauts logo.

Overall, the clothes at Cowboys and Astronauts are high-energy, adventurous, and welcoming, just like the shop itself. 

Stock Mfg. Co

This custom boutique offers the best in utility-chic casual styles and custom workwear. Stock Mfg. Co has been designing personalized work clothes for the high-end hospitality industry since 2012.

We’re talking places like Soho House and GT Prime. In 2015, they opened they’re West Fulton showroom, an efficient combination of industrial-modern and Chesterfield-sophistication.

If you’re looking for fashionable utility shirts or practical but modern outerwear to go with your Timberlands or Danners, Stock Mfg. Co has more bespoke options than any store in Chicago.

If you’re a mixologist or field worker who doesn’t want to sacrifice style for function, they’ve got you covered too. Even their aprons are fitted and chic.

Their roots in functionality aside, Stock Mfg. Co offers casual hip menswear for any type of guy. Did we mention that their lofty and rustic showroom includes a billiards table and a bar? Grab a complimentary drink or two while you shop at this Esquire and GQ-approved boutique.

Daniel George Custom Suits

Daniel George started designing menswear in the 90s, inspired by British and continental European fashion. What separates this clothier from other upscale suit shops is that they forgo the stuffy intimidation factor, but not the quality and excellent attention to detail.

Their goal is to help you find your best formally-dressed self, whether you’re trying to maximize a budget or looking to acquire a hand-made Loro Piana. Daniel George offers a modular approach, featuring several construction options, fabric specials, suit styles, and payment options.

If you want to hit several birds with one stone, they’ll even offer personalized service to build a high-value custom wardrobe with different tiers of discounts depending on your final curation.

Imagine how helpful this is going to be after a big promotion that ensures you’ll be needing many more suits, or if the airline loses your luggage.

Another testament to their down-to-earth service is that you consult with Daniel George himself during the suit-acquisition process. He and his two highly-skilled tailors are known to turn the stressful process of buying expensive clothes into an educational and non-judgmental exploration.

If you’re looking for clothes for a formal wedding, prom, or a big business trip, Daniel George is an uncharacteristically unpretentious option for this caliber. They democratize the world of high-end formalwear without watering it down.

Mildblend Supply Co.

This Wicker Park gem offers a universe of jeans, from classic Levi’s to modern-fit Naked & Famous pants. In fact, they’re one of just three Chicago partners of the latter brand, even carrying the limited edition Batman-inspired denim pieces that boast custom buttons and detailed embossed leather patches.

Founder and fashion industry long-timer, Luke Cho, opened this go-to denim outfitter in 2011, quickly becoming a Chicago staple. Unlike the common limited boutique approach, Cho ensures a department store-level of denim offerings, though still curated for style and excellence.

There’s a pair of jeans for every guy on the racks.  

Mindblend Supply Co. even provides jeans-specific tailoring services. Their onsight artisans, including Cho himself, professionally darn substantial holes and rips. They offer chain stitch hemming to get you the perfect length fit, or if you’re looking for a convenient permanent cuff.

This hip boutique also sells sunglasses, outerwear, fine leather goods, and other practical but stylish pieces for your closet, all at reasonable prices. I saw a pair of Wolverine duck boots for under $120 there once.

The space itself is fittingly rustic and recycled, and their team has a reputation for their knowledge and laid-back, friendly service. Head over to Mildblend Supply Co. if you enjoy finding heritage brands, up-and-comers, and Chicago local designers all in one space.

RSVP Gallery

RSVP Gallery is the yang to Gallery Aesthete’s yin. It’s a conceptual experience for fashion-loving men featuring many store exclusives, but with a colorful Pop Art tone.

In addition to high-fashion brands like Comme des Garçons and Phillip Lim, you’ll find trendy streetwear lines like Bathing Ape and Needles, and classic athletic names like Nike and Adidas. Check out their site to see all of the brands they carry.

We aren’t referring to standard Nike track suits here though. Sift through RSVP’s lively racks, and you’ll find pieces from Nike’s partnership with Kim Jones, the men’s artistic director for Fendi and Dior.

Some stand-out pieces include the Nike X KJ crewneck sweater, a popular piece with the luxury kicks crowd, and their practical and uniquely-shaped hooded jacket in obsidian.

Jay-Z’s Just Don hat and the Martine Rose oversized floral-print denim jacket are other fashion-forward pieces stocked on the shelves.

The gallery also conducts raffles for coveted few-of-a-kinds, like the Air Fear of God Triple Blacks, a high-performance sneaker designed with modern lines appropriate for a futuristic runway. 

RSVP Gallery, and their neon-lit showroom, is Chicago’s premium experience for men who are a little artistic and a bit indie. It’s also a great place for those looking for stylish athletic wear that can take them from brunch to the gym.

BLVDier

This posh suit outfitter was founded by custom clothier, Zach Uttich, in 2014. They’ve quickly become one of Chicago’s premier formal shops offering fabrics from Delfino, Loro Piana, Distef & Quaregna, Ermenegildo Zegna, and more.

Despite this excellent and upscale sourcing, custom two-piece suits start at a reasonable $950.

Unlike many made to measure shops, BLVDier also provides high-quality made-to-order items. They offer shirts of many collar styles and an Italian carded flannel made from Vitale Barberis Canonico’s 270gr fabric.

This means it’s thick enough to be worn as a shirt or used as outerwear. They also have handsome pea coats, dress coats, and a quietly avant-garde deconstructed dress coat.

And if you want to learn more about dapper dressing, check out their website blog, a visual education on everything from the tuxedo to tweed. BLVDier is the perfect local gateway into real clothes, away from fast-fashion suits.

Conclusion

Though many may not know it, Chicagoans are fortunate enough to have a wealth of men’s fashion stores.

Looking for a suit? BLVDier and Daniel George give even the most upscale Madison Avenue clothiers a run for their money. A pair of jeans? Mildblend Supply Co. has you covered.

Chicago’s men’s clothing stores are as diverse as its people. No matter which of these outfitters you go for, you’re bound to get some good stuff.