This weekend, Lollapalooza celebrates its 10th year in residence at Chicago’s Grant Park, and in the event that you’re making the trip to the Windy City, we thought we’d help guide you the best way we know how…

By finding you the best menswear shops to visit while you’re in town.

073014_Chicago-Apt-9The Shop: Apartment Number 9
The Stop: For all things #menswear, this place is plugged in—with everything from designer suits to tailored sweatpants.
The Spot: 1804 N Damen Ave

073014_Chicago-HaberdashThe Shop: Haberdash
The Stop: For the modern take on traditional menswear—and they’ve got their own line of suiting, sportswear and Italian cotton polo shirts.
The Spot: 607 N State St

073014_Chicago-IndependenceThe Shop: Independence
The Stop: For your Americana fix. They’ve got everything from Gitman Vintage shirts to turquoise belt buckles.
The Spot: 47 E Oak St

073014_Chicago-JackSpadeThe Shop: Jack Spade
The Stop: While you’re on the way out of Independence upstairs, stop into Jack Spade downstairs (they’re in the same building).
The Spot: 47 E Oak St

073014_Chicago-GeorgeGreeneThe Shop: George Greene
The Stop: Also in the same building as the last two, round out your one-stop shopping with the elder statesman of Oak Street menswear, George Greene, whose selection of Charvet ties is a sight to behold.
The Spot: 49 E Oak St

073014_Chicago-TomFordThe Shop: Tom Ford
The Stop: Well, you’re already on Oak Street. Plus, you might need to pick something up for your dear friend Jay Z.
The Spot: 66 E Oak St

073014_Chicago-SuitsupplyThe Shop: Suitsupply
The Stop: For a quick wardrobe upgrade en route to dinner with your new record exec friends.
The Spot: 945 N Rush St

073014_Chicago-MeyvnThe Shop: Meyvn
The Stop: For really nailing that Lollapalooza vibe—the right way, not the neon tank top way—with laid-back denim, leather jackets and classic sneakers.
The Spot: 2627 N Kedzie Ave

073014_Chicago-J-Crew-LudlowThe Shop: J.Crew Ludlow Shop
The Stop: For your go-to when you’re not sure whether you’re in the mood for just a chambray shirt or a full-on new suit.
The Spot: 900 N Michigan Ave


  • Kempt Staff