Our first look at men’s shopping in Chicago covered the venerable Oxxford Clothes, hatmaker Optimo and others. Part two has the goods on a #menswear specialist and some more old-school purveyors.

Haberdash
607 N. State St.
312-624-8551
[email protected]

One of a bunch of new haberdashers that have emerged onto the scene in the last few years.  I’ve listed their newer store, since it’s a little closer to the rest of the things on this list, but their Old Town location was ahead of the curve, opening its doors in 2005.  If you’re a hardcore #menswear guy, this is going to be Mecca for you.  Alden, 3Sixteen, Filson, Gant, LBM 1911, Steven Alan, and Woolrich are just a few of the oft-lusted-after brands they stock.  There is also EDC shop, next door to the location listed above, which features exclusively footwear, accessories, and grooming products.  All in all, a can’t-miss if you’re in town for a short stay.

Haberdash's State Street digs.

Jack Spade
47 E. Oak St.
312-915-0315

Literally just downstairs from Shrine, it would be foolish not to pop in if you’re already on Oak Street.  Jack Spade has only a handfulof stores, most on the East Coast, and offers a great selection of functional basics that are classic without being humdrum.  The briefcases and messenger bags are a personal favorite of mine.  Plus the people who work here are great and really love the brand.  You don’t feel like they’re there to get a paycheck but to share something they love with anyone who will listen.  And that’s what I’m looking for in retail.

Paul Stuart
107 E. Oak St.
312-640-2650

One of the most elegant mens stores you’ll find anywhere.  The store is cozy (small, but in a good way), the guys who work there are extremely stylish for the most part, and I unabashedly think Paul Stuart always has some great stuff.  Their giant selection of silk knit ties in a reasonable width, many colors with the option of woven spots, are a standby for me, as are the other colorful accessories.  Tip—their travel umbrellas are a great buy if you need something that looks good but fits in a carry-on bag.  There is also a smaller Paul Stuart on LaSalle, but unless you just want to pop in after a visit to the Art Institute, I recommend going to Oak Street.

Ralph Lauren
750 Michigan Ave.
312-280-1655

Sure, you can buy Ralph Lauren stuff pretty much anywhere in the world, including your couch, but his grand stores are undeniably awesome.  This store is actually larger than any of the New York stores, features more than one palatial staircase, all the usual wood paneling and oil paintings, as well as a top-notch selection of vintage goods.  If you’ve been hunting for a 50-year-old Patek in near-perfect condition, look no further.  Also next door is the the RL Restaurant, my favorite re-fueling spot in this part of Chicago.  It lacks the commercial-extortion feel of most restaurants in the Michigan Ave. area, instead feeling like a club in the 1920s.  Service is out of this world, rivaled only by the food.

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.

Oxxford Clothes
1220 W Van Buren St. #7
312-829-3600

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.

Chris Despos
34 E. Oak St.  #3
312-944-8396
[email protected]

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.

Rack city at Despos.

Optimo Hats
320 S. Dearborn
312-922-2999
[email protected]

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.

Shrine Haberdashers
47 E Oak St
312-675-2105
[email protected]

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
630-664-6209
[email protected]

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.