A sports jacket isn’t a suit, so don’t treat it like one. A plaid shirt, purple sweater, anything from khakis to jeans—it all works. If you’re uncertain, compose the outfit on your bed until you get it right. (We won’t tell anyone, promise.)
Jacket, $2,480, and pants, $615, by Brunello Cucinelli. Sweater, $125 by Michael Kors. Shirt, $195 by Black Fleece by Brooks Brothers. Tie, $75 by Gitman Vintage. Pocket square, $45 by Michael Bastian. Portfolio, $1,380 by Louis Vuitton. Shoes, $995 by Ralph Lauren. Socks, $29 by Smart Turnout.