Chicago

The two moods men are most comfortable projecting are sporty and smart-ass, but the t-shirts that express those moods can only be worn in polite company if the polite company's blind, and not particularly handsy. Class up those sentiments, with Red Jacket Shop.

Named for a Seneca chief (his actual signature = their logo), Red's a burb e-tailer that's bumped sport-and-smirk up a wardrobe rung to smartly designed polos, acceptable anywhere that hasn't banned you for reasons other than attire. Some athletic highlights: baseball (two-toned polos w/ classily embroidered team crests); college (twill-collared orange & blue rugby shirt w/ Illini "I" + championship year sewn on crest); tennis and golf (the plaid-shouldered, Italian-made "30 Love"); and soccer (Wash Diplomats 1974 polo w/ regal red & blue sash). Wise-guy offerings from the “vintage destroyed wash”, 100% cotton “Outsider” polo collection come with poignant sayings scribed artfully on the side, from the wittily besotted (“A Bartender Is A Pharmacist With A Limited Inventory”) to the cheekily violent (“Those Who Live By The Sword Get Shot By Those Who Don't”) to the Bozo paranoid ("Can't Sleep, Clowns Will Eat Me").

Red also slings a range of track jackets, sweaters, and hoodies, and even their tees transcend, whether it's straight up, distressed, and "snow washed" college shirts (from Wisconsin to Hawaii) or semi-esoteric stuff like "Painless", a faded plum portrait of a sumo squad -- which may seem to convey "sporty", but actually just professes your third favorite mood, your love of esoteric underwear solutions.