Your first instinct will be to pair your new plaid suit with a white shirt and a solid dark tie. Ignore that instinct—the fresher, funner approach is to wear it slightly left of center. Steer into the swerve with a striped tee and Chelsea boots, or a turtleneck and gleaming white Adidas. A plaid suit should always be the loudest thing you're wearing, but that doesn't mean everything else has to be on mute.

Suit, $1,625, by Black Fleece by Brooks Brothers

Shirt, $475, by Michael Bastian

Tie, $115, by Ralph Lauren

Shoes, $985, by O’Keeffe

Socks, by Etiquette Clothiers

Tie Bar, by The Tie Bar