Chicago is a pretty classic city. Not classic like London, with its tailoring trade and aristocratic propriety. And not like Florence, where every cobblestone and sport coat is imbued with history and tradition. It’s classic in a way that’s equal parts rugged Americana and serious business.
At the turn of the twentieth century, Chicago was at the heart of the American garment trade, and more specifically, the American ready-to-wear menswear explosion. It was not long ago that men switched over to ready made clothes, and Chicago was a catalyst for that switch—urban legends claim one in three garments in the U.S. passed through Chicago.
But Chicago’s history doesn’t weigh it down. Horween Leather (founded 1905) and Oxxford Clothes (1906) sit alongside newcomers like Haberdash and Optimo Hats. Chicago’s merchants seem to share a passion for authenticity and giving customers an experience along with a product. Whether it’s a custom-fitted hat from Optimo or a chat about tie patterns with the gents at Shrine Haberdashers, you’re getting service and substance for your money.
Below is a brief guide to what Chicago has to offer the guy looking for the best. And often the best he can’t get anywhere else.
1220 W Van Buren St. #7
So this isn’t a store per se, though you can give them a call and set up made-to-measure appointments here. Oxxford produces arguably the finest factory-made suits around—on par with anything from the better-known Kiton, Attolini, etc. Honestly, there is more hand-work in an Oxxford suit than in some bespoke suits, although it’s not without its cost. If you’re a tailoring nut, it’s worth giving them a call and asking if you can drop by to check things out.
34 E. Oak St. #3
Chicago used to have a plethora of great bespoke options. It was just as good, if not better than, New York when it came to fine tailoring. But things have changed a little in the last two decades. As far as I know, Chris is the only guy producing a real bespoke suit to Savile Row level standards in Chicago. This includes cutting a paper pattern for each client, followed by as many fittings as it takes to get things perfect (generally three-ish for a first suit). He is making me a suit right now, and you can follow the process on Simply Refined to take a look and see if you think it might be for you.
320 S. Dearborn
Optimo is one of the few great hat stores left, not in this country, but in the world. If you want, they can bust out the torture-device-esque hat measuring tools and build you something from the ground up, custom fitted to you alone. Or you can always go for an off-the-shelf staple. The cost is not low, but like a suit or great pair of shoes a proper hat is made to last a lifetime. I’ve provided their downtown location, but there is also a Southside location for those who would prefer to stay out of the main shopping district.
47 E Oak St
This is the other must-see haberdashery in Chicago. Nestled on the second floor of an Oak Street townhouse, Shrine is a cool mix of off-beat brands you might not have heard of and tried-and-true favorites like Drake’s and WANT. Ok, so the over-sized rings might not be my thing, but the store really represents the personalities of the guys who run the show. Stop in, have a chat about clothes, and maybe pick up something that no one else back home will have seen before. These guys celebrated their first anniversary in November, and here’s wishing them a good sophomore year.
Oak Street Bootmakers
No storefront here. But the shoes are all designed in Chicago by a second-generation cobbler, made out of Horween’s Chromexcel leather, and feature full welts that allow your shoes to be resoled. Heads and shoulders above the other camp mocs and work boots you find in most stores. Prices are competitive. Order online or give them a call if you need to chat about styles, stock, or anything else.
Part II deals with more classics and more newcomers.
Stephen Pulvirent also writes at his blog, Simply Refined.