A Cooler Baseball Jacket

You want a baseball jacket, not an ill-fitting pleather-sleeve letter jacket. Get one that's streamlined—in a superthin nylon or leather that barely skims the frame.

Straight-Leg White Jeans

You know that rule about breaking out white only after Memorial Day? Forget it. Just keep your white jeans straight (no boot-cuts, please) and you can rock 'em year-round with just about anything.

Jacket, $1,030, by Dior Homme. V-neck with shirt inset, $410, by Brunello Cucinelli. Jeans, $70, by Levi’s. Shoes, $795, by Ralph Lauren. Belt by Billykirk. Watch by Omega.