Best Men’s Wear Clothing Stores In Chicago

October 4, 2010 4:57 PM

Men either struggle with fashion or know what they want. Enhancing a man’s wardrobe can be a trying task for some, but this list makes the task easier. Check out some of the hottest stores in town whose goal is to make men more appealing. – Renita S. Manley-Garrett


1350 North Wells Street
Chicago, IL 60610
(312) 440-1300

Haberdash, located in Old Town, is dedicated to the all-around traditionally modish, yet cool American guy. This one stop shop has everything men will need from nifty socks to an assortment of well-designed and attractive ties and handkerchiefs. Haberdash also offers a great selection of shoes including the award-winning designer John Varvatos and the American classic, Timberland Boot Company. Modern twists to the orthodox clothing offers Chicago men a welcomed option to the standard suit and tie look. A second location is coming soon to 607 State Street.

Paul Stuart

107 East Oak Street
Chicago, IL 60611
(312) 640-2650

Upon entering Paul Stuart, you’ll feel just like the clothing: grandiose. With only one other location in Manhattan, New York, Paul Stuart is the epitome of luxury, style, and elegance for men. Sea Cotton dress shirts and cashmere or lamb’s wool sweaters are simply a few of the power-dressing clothing items at Paul Stuart. Finely crafted accessories, a beautiful array of colorful ties and its made to measure custom suit tailoring department make this establishment a must for your distinguished gentleman.


1329 South Michigan Avenue
Chicago IL 60605
(312) 431-1900

Succezz, located in the South Loop, is an Urban loft style boutique that offers its staunch customer base the best of street wear attire. Owners Bobbie Simmons, Chicago native and NBA player, and LaVelle “V-Dot” Sykes envisioned a boutique that would highlight the best in hip urban wear. Besides their own Brand, Succezz, this boutique offers Grind Stone, Levi, and T-shirt designs by Chicago designers Chi-Boyz. Succezz also has an exclusive contract with Nike, enabling them to carry designs you won’t find anywhere else. Exposed brick, an inviting lounge area, and top-notch customer service makes this a welcoming, energetic boutique.

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Apartment 9

1804 North Damen Avenue
Chicago, IL 60647
(773) 395-2999
Facebook: Apartment Number 9

This mainstream, yet contemporary boutique doesn’t aim to be cutting edge, flamboyant, or glitzy. By way of brand names such as the longstanding Paul Smith and the vastly popular Band of Outsiders, this boutique beckons the covert stylish man. An appropriate blend of neutral colors, plaids, button ups, and casual leather jackets dominate this casually fresh boutique.

Syd Jerome Men’s Wear

2 North La Salle Street
Chicago, IL 60602
(312) 346-0333

You can’t help but to marvel at the always updated and eye-catching window display at Syd Jerome Men’s Wear. Located in downtown Chicago, this men’s wear clothing store encompasses a variety of apparel. Armani suits, clothing by the Italian line Etro, Polo, and the always elegant Oxxford are a few of the swanky brands that make Syd Jerome prodigious.

Sids Clothing and Hats

609 West Roosevelt Road
Chicago, IL 60607
(312) 421-3332

Looking for a brilliant hat and coat combination for the cold months? Then Sids Clothing and Hats is a must visit. Their hats, coats, and apparel appeal to men from all walks of life: from Wall Street to Beat Street. With over 5,000 different styles of hats from which to choose, Sids Clothing and Hats is the premier destination for the fashion forward man looking to top off his ensemble.

Entourage Man

1355 South Michigan Avenue
Chicago, IL 60605
(312) 353-2300

This suave South Loop boutique is full of impressive designs by brands such as Avva, Robert Graham, Sand, and a host of other inventive indie designers. This urban, chic boutique also carries an impressive selection of staggering shoes including Mark Nason, Jump, and Bacco Bucci. Willie Davis and Stephen Thurston, the owners of Entourage Man, believe that a man’s fashion should be intriguing, distinctive, and should surpass impressive, making their motto “style beyond desire” utterly true.


50 East Oak Street
Chicago, IL 60611
(312) 266-4949

Tessuti is one of the premier destinations for grandiose Chicago men and young men looking for stylish suits and up-to-date men’s fashion with apparel inclusive of casual, classic, and urban wear. This boutique boasts a huge assortment of vibrant ties and other striking accessories. Tessuti prides themselves in customer service, custom made suits, and offers tailoring on site to ensure a proper fit.

His Stuff

3162 North Broadway Street
Chicago, IL 60657
(773) 281-6111

His Stuff offers attire for men who are in touch with their inner fashionisto. The clothing in this boutique can be gaudy, or casual, but they will never be outdated. Fashionable underwear, mod men’s blouses, unique accessories, and the popular brand Fluxus, designed by Project Runway’s Jeffrey Sebia, have found their way onto the racks at His Stuff.

Balani Clothiers

Flagship Store
55 West Monroe Street
Chicago, IL 60603
(312) 345-1535

Buying suits off the rack can be a challenge. Hence, the beauty of Balani Clothiers. Balini Clothiers custom makes suits, shirts, and tuxedos to flawlessly fit any man’s distinct physique. Their well known for their down to earth customer-service, but still offer topnotch expertise. You won’t have to struggle anymore with those hard to find half sizes or ill-fitting suits after you’ve had your custom made, debonair suits from Balini Clothiers.

Renita S. Manley-Garrett is a Chicago and Chicago-land based Image/Wardrobe Consultant and the owner of Revamped Image Consulting. She specializes in personal shopping, styling, and offers a variety of image and wardrobe based services. Visit her website at

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