Gear: Public I
1923 W Division St, (773) 772-9088
Order at PublicIFashion.com
This spot's done as much good for Chi's style rep as Ferris Bueller's beret's done to destroy it. With everything from retro Bears apparel to designers like Z Brand, you'll be dapper enough to move more sausage than Abe Froman.

Drinks: Sam's Wine & Spirits
1720 N Marcey St, (800) 777-9137
Order at SamsWine.com
With 20,000 different bottles for sale, Sam's is Chicago's premier enabler. Their website offers descriptions, ratings, aggregated magazine recommendations, even pictures -- for the man whose thirst is as powerful as his illiteracy.

Footwear: City Soles/Niche
1566 N Damen Ave, (773) 489-2001
Order at CitySoles.com
High-end City Soles and even higher-end Niche share both brick-and-mortar and online space, creating a single-stop solution for discerning footists. CS carries leading-edge, imported, and exclusive kicks from the likes of Espace, Tsubo, and Royal Elastic, while Niche offers a pair of tan Mark Nason boots adorned with a raised cross -- sure to make you the envy of friends, and fashion-forward monks.

Food: Giordano's Pizza
9415 W Higgins Rd, (800) 982-1756
$15.25 to $20.80 from Giordanos.com
Ask any Chicagoan where to get the best deep dish pizza, and he'll belch in your face, then animatedly describe your grimace to fellow Giordano's lovers over a slice. The vaunted parlor partially bakes, then freezes their double-dough 12" masterpieces before shipping them UPS Next Day Air -- so you can finally burn down your local Pizzeria Uno without experiencing any pie interruption whatsoever.

Furniture/Accessories: I.D. Chicago
3337 N Halsted St, (773) 755-4343
Order at IDChicago.com
Selling both contemporary designs and retro furnishings that were ahead of the curve 40 years ago, I.D. C's the source for shape-defying chairs, sophisticated couches, and tables so sexy you will make love on them, and to them. IDC also sells personal effects, like unusual cufflinks and perforated Italian leather wallets inspired by racing gloves -- providing literal wallet holes to match the figurative ones that recently forced you to sell off your gold fillings.