All-encompassing Gear: Guise|Chic
'til Aug 31 at 2128 N Halsted St, between W Dickens & W Webster; Lincoln Park; 773.929.6130
All spring & summer's 60% off, including shorts, swimsuits, tees, polos, and short- and long-sleeve buttondowns from the likes of Oliver Spencer, Hartford, Acne, Duckie Brown, Unruly Heir, Rag & Bone, Theory, Edun, Gilded Age, Ever, Filippa K, and Steven Allan. For an additional 20% off sales items, get a haircut in one of Guise's four luxe barber chairs, completing the perfect guy afternoon of clothes shopping and hitting the salon. Weeee!
Get fully styled at GuiseChic.com
Flossing Gear: p&L Boutique
Sat thru Aug 31 at 2956 N Clark St, between W Oakdale & W Wellington; Lakeview; 773.248.3758
Up to 75% off all spring/summer gear, including denim by Guido and Mary, Chevignon, 1921, and Lifetime, plus hoodies and windbreakers by Le Coq Sportif, Industry, and Art In The Age Of Mechanical Reproduction (Skynet is self aware. And is ready to screw.)
Peep the goods at pAndLChicago.com
Denim Gear: Hip Fit
1513 W Foster Ave, at N Clark; Ravenswood; 773.878.4447
Up to 60% off the entire spring/summer stock of Kasil, Buffalo David Bitton, and Blue Cult jeans, Neves belts and buckles, and Heavy Rotation tees, whose musically nostalgic designs range from ghetto blasters to "Not Getting Any Younger" -- a mix tape sitting forlornly in a chair, wishing someone would slide him into a ghetto blaster.
Be hip at HipFitChicago.com
Outdoor Gear: Patagonia
'til Aug 21 at 1800 N Clybourn Ave, at N Sheffield; Sheffield/DePaul; 312.951.0518
The activewear empire's offering 40-60% off fleeces, buttondowns, tees, cords, waterproof pants, belts, sneakers, boxers, briefs, and five styles of raincoats (thankfully none of them claiming to be "edible").
Get outdoorsy at Patagonia.com
Upscale Gear: Gamma Player
'til Aug 20 at 2035 W Division St, between N Damen and N Hoyne; Ukrainian Village; 773.235.0755
50% off most summer gear including Rico nylon jackets in four colorways (sky blue, black, dark green, purple), Firma short-sleeve stretch cotton shirts, Merchant Drapier high-neck polos, and Chris & Tibor leather duffles -- which, if employed stealthily, can get you 100% off on everything else.
More Flossing Gear: Trend For Men
1551 N Wells St, between W North and W Burton Place, Old Town; 312.867.7700
Snag 30% off short- and long-sleeve buttondowns from English Laundry and Fender, plus graphic tees from Dragonfly and True Love & False Idols (the real-life story of a disenchanted Billy groupie?).