Really Cheap Gear: Haberdash
1350 N Wells St, at Schiller; Old Town; 312.440.1300
The Old Town mainstay is slashing as deep as 80 percent on kicks from K-Swiss and Gola, swank Spring jackets, shirts and trousers from Theory, Penguin, Trovata, Shipley and Halmos, and VelvetMen, a club Costanza would've totally joined were it socially acceptable.
Take a peek at HaberdashMen.com
Swank Gear: Barneys New York
At Barneys, 15 E Oak St, at Rush; Gold Coast; 312.587.1700
They're dropping 50 percent from notably classy Spring/Summer lines like Alexander McQueen, Christian Dior, and Burberry, which tastes like cotton, but has a ton of antioxidants.
Gaze on the fashion at Barneys.com
Funktastic Gear: Funkshion (Now Closed.)
2121 W Division St, btw Leavitt and Hoyne; Wicker Park; 773.697.4119
Snag yourself up to 50 percent off on sleek dark button downs and jackets from TWN Black, sexified tees from TiT2, South Beach-style tees from Anthony Vega, and denim from Robin's and Laguna Beach, which you'll pretend to hate, but TiVo nonetheless.
Bring your funk to FunkshionClothing.com
Tee'd Up Gear: Hip Fit (Now Closed.)
1513 W Foster Ave, at Clark; Andersonville; 773.878.4447
Mention Thrillist through this weekend and be rewarded with 25 percent off all T-shirt goodness: Basics from Alternative Apparel, cleverly cartoonish Loyal Army, artily sustainable Fluffy Co, and eclectically sweet Heavy Rotation, which also describes the clothes that spurred you to make these purchases.
Fit yourself hiply at HipFitAndersonville.com
Soleful Gear: Solemates
2708 N Halsted St, at Schubert; Lincoln Park; 773.327.7782
The hubby and wife-owned Lincoln Park boutique is taking 25-50 percent off colorfully eccentric Nooka watches, denim and outerwear from Cheap Monday, and street-credibles from Brooklyn Circus and Public School, mercifully covering up your North Shore Country Day back tat.
Get some at SolematesChicago.com
Sleeved Gear: Riley
1659 N Damen Ave, btw Wabansia and Concord; Bucktown; 773.489.0101
They're knocking 20 percent off styling men's button downs from the likes of Rufus, Ted Baker, 7 Diamonds, Cockpit, and Arbitrage, something you'd know little about, what with your weak-ass bond portfolio. Ooohhh burn!!!