607 N. State St.
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.
47 E. Oak St.
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.
107 E. Oak St.
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.
750 Michigan Ave.
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.