While top fashion houses—including Gucci, Hermes and Tommy Hilfiger—turned out wild plaid dinner jackets for Spring/Summer 2012, it wasn’t until Don Draper donned the style to a Connecticut dinner party (in “Mad Men” Season 5, Episode 5) that it reached its trendy peak. True, it was a tad unsettling to see the informal layer on the typically elegant character, but it obviously served as sartorial inspiration to gents tired of their go-to black, brown and navy jackets. A number have already begun boxing themselves into slim, classic incarnations for both work and play. This season, buy into the look—and take it from collegiate to rugged to polished with the mere switch of a few separates. Every once in a while, be sure to go full-on “mad” in an outfit that screams “Draper;” a loud plaid blazer paired with a white shirt and a skinny tie is retro, and it works.
 Go Bold for Boys’ NightJohn Varvatos Star USA jacket, Earnest Sewn tee and Hudson jeans available at Moris Fashions, Central West End, 314.361.6800.
 Go Bolder for Brunch
Isaiah Ciarrai blazer, TailorByrd linen shirt and Ivory denim available at Woody’s Mens Shop, Frontenac, 314.569.3272.
 Go Boldest for the Boardroom
Samuelsohn blazer, pants, shirt and tie available at Mister Guy, Ladue, 314.692.2003.
John Varvatos Star USA jacket, Earnest Sewn tee and Hudson jeans.
Samuelsohn blazer, pants, shirt and tie.
Photo credit: Carmen Troesser