Everything Gear: Guise|Chic
2128 N Halsted St, between Dickens and Webster; Lincoln Park; 773.929.6130
All fall/winter's 40-60% off, including outerwear from Filippa K and Oliver Spencer; buttondowns from Duckie Brown and Steven Alan; TSE and Nicole Farhi sweaters; Gilded Age, Nudie, and Acne denim; Theory suits and dress shirts; and C.P. Company dress pants. Bonus: 'til Jan 31, buy two 40% off items and get any 60% off item free -- a total savings of 16000%. As far as you know.
Check sale-io at GuiseChic.com
Flossing Gear: p+L Boutique
Today-Jan 18 at 2956 N Clark St, between Oakdale and Wellington; Lakeview; 773.248.3758
25-75% off everything, from fedoras, skullies, and messengers from Goorin Brothers, to Nobis winter hats, to Insight blazers and tees, to Station 8 buttondowns, to canvas & leather sneaks from Tretorn -- who've shod Bjorn Borg since the 70s, but claim no responsibility for that headband.
Peep it at PAndLChicago.com
Smooth Gear: Apartment Number 9
1804 N Damen Ave, between Churchill and Willow; Bucktown; 773.395.2999
40-75% off outerwear from Dries Van Noten, Philip Lim sweaters, Rogan denim, Martin Margiela upscale sneaks, and suits from Band Of Outsiders (though if you're such an outsider, why the suit?).
Feel the cheapness at ApartmentNumber9.com
Rocker Gear: Bonnie & Clyde's
1751 W Division St, between Hermitage and Wood; Wicker Park; 773.235.2680
All men's is 40-50% off, e.g., Wrath Arcane's subtly menacing outerwear, Love Brigade pullovers, Cassaves outerwear and denim, Union buttondowns and henleys, and blazers and dress pants from Sylvain Sylvain -- founded by the New York Dolls guitarist, because who knows dress pants like...a guy who wears dresses?
Get your Warren Beatty on at Bonnie-Clydes.net
Home Gear: Design Within Reach
1574 N Kingsbury St, between North and Weed; Lincoln Park; 312.482.8661
10 E Ohio St, at State; River North; 312.280.4677
Up to 60% off uber-modern bar stools, coffee tables, bookcases, and "Flying Vee Shelves", thin metal wall-mountable Vs ideal for storing books, curios, or books you're just not that curios about.
Eye gorge at DWR.com
Swank Gear: Haberdash
1350 N Wells St, at Schiller; Old Town; 312.440.1300
Almost all fall/winter's 50% off including jackets, sweaters, blazers, pants, wovens, and buttondowns from Trovata, Theory, Vince, John Varvatos Star, and Ever, the perfect call if Never Have You Ever.
Get dashing at HaberdashMen.com
Accessory Gear: Riley
1659 N Damen Ave, between Wabansia and Concord; Bucktown; 773.489.0101
20-50% off Property Of wallets & messengers, Coal knit skullies, Arbitrage and TailorByrd buttondowns, Canterbury of NZ v-neck sweaters, and dress shirts and pants from Ted Baker.
Click it at ShopRiley.com
Preppy Gear: The Original Penguin Store
901 N Rush St, at Delaware; Gold Coast; 312.475.0792
Take 40% off fall/winter goodness like dress pants, tees, polos, buttondowns, vests, sweaters, hoodies, jackets, and one special track jacket dubbed "The Ratner", available in "chive" -- appropriately, the same color that rocketed from your mouth while watching The Family Man.
Waddle at OriginalPenguin.com
Work Gear: His Stuff
3162 N Broadway, between Belmont and Briar; Lakeview; 773.281.6111
5314 N Clark, between Summerdale and Berwyn; Andersonville; 773.989.9111
Up to 40% off outerwear from Hugo Boss Red and Swiss Army, 7 Diamonds buttondowns, Modern Amusement cardigans and v-necks, J Lindeberg dress pants, and Grenson dress shoes and chukka boots. ("Chukka boot. Chukka boot. Let me love you let me rock you..." Jesus Christ we're sorry.)
Get yours at HisStuffChicago.com