This month we’re giving you 28 ways to layer up in this crazy weather. Up today: a check dress shirt in sophisticated, urbane colors.

The problem with a check dress shirt is that it can look a little college bro if not styled properly. Wear one in preppy, athletic hues like cobalt, orange, or red, and with a big, fat tie, and you might come off a little bit like a sportscaster. Not unstylish per se, but maybe not as refined or slick as you truly are on the inside. For a way to do the check shirt with a slightly more high-gloss, urbane finish, reach for styles in strong brown and black. As Jason Sudeikis proves, above, it reads more like man in charge, than man who loves Croakies, while still offering up that graphic punch that makes a check dress shirt so desirable in the first place. We especially like it with a slim tie (2.5″ or so wide) in a highly textured fabric like linen or wool knit to keep the preppy vibes even further at bay.

Here, five excellent options to get you started.

brooks brothers.jpg

Brooks Brothers, $92, available at


Suitsupply Brown Check Shirt, $79, available at


Maison Margiela, $395, available at


Barba Checked Shirt, $113 (Was $173), available at


Isaac Mizrahi, $20 (Was $60), available at