Tommy Hilfiger, $99.50
As the days get longer and warmer, your style should be more relaxed, but it shouldn't go away entirely. Cut from breathable cotton with half or no lining, this season's featherweight blazers are the perfect cover for cool spring days and brisk summer nights. Unstructured options like these should fit like a good pair of jeans—trim, yet relaxed and better looking after a few hardy wearings. They're made to be a bit rumpled, which means the rest of your look should be pulled together. A crisp button-down and some canvas sneakers? Good. A wrinkled linen shirt and flip-flops? Bad.
J.Crew,
$148
Boss Orange,
$275
Rugby,
$178
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