Culture + Style

Dapper Dons: Where Guys Get Their Swag in Chicago

Suitsupply (Photo: Ten Photos)

You’re a man on the go. With as many business trips as you take each month, you have packing down to a science. In fact, your carry-on is so light, you almost forget it’s wheeling behind you. But you’ve arrived to town and received a last-minute invite to a swank event where Kanye is rumored to show up for a quick set (you know he won’t, but just go with it — at least there will be free drinks).

Then you realize you forgot to pack a blazer (hey, this was a breezy in-and-out trip with a new startup at 1871 you’re pitching — no jackets required!) and then you look in the mirror and decide your hair could use a clean-up. You have a couple of hours between your last meeting and the dinner: Where do you go? Don’t stress. We’ve got you covered.

316 Club Barber Spa


316 Club Barber Spa (Photo: Ten Photos)

You had us at shave and a beer. Thankfully, you’re the one drinking and not the guy with the straight-edge razor against your throat. At this men’s grooming club in the heart of the Loop that was designed to reflect an old school Vegas club, you can get a haircut, shave, shoe shine, eyebrow wax and more while playing pool on a red felt table, sipping a beer (or BYO whiskey) and hanging with the guys on leather club chairs in front of a fireplace while watching the game on a flatscreen. Memberships or drop-ins welcome.


best-mens-shop-chicago-suitsupply-03.jpgSuitsupply (Photo: Ten Photos)

You’re all about bespoke suits, clearly. Sometimes you need to buy off the rack and still look like you had it made just for you. The modern-designed, light and airy off-the-street shop in Chicago’s swank Oak Street shopping district has everything you need — including a friendly, non-pushy staff. With slim cuts, fresh designs and beautiful Italian fabrics, their suits, sport coats, shirts, shoes and accessories will have you feeling like a million bucks, even if you only have to spend a few hundred.


best-mens-shop-chicago-haberdash-02.jpgHaberdash (Photo: Ten Photos)

This one-stop shop blends a shopping experience with some old-world charm and even a straight-edge shave if you fancy it. The 10-year-old boutique has everything a guy needs like raw denim, hip blazers, sleek outerwear, kick-ass boots, grooming products, bags and more Look for well-curated brands like Alden, Barbour, Gitman Bros., Shinola and Mason’s. Even if you don’t know those names, you’re going to love wearing their duds.

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