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The short-sleeved button-up has been getting a lot of attention now that it’s too muggy for oxford shirts, but it’s a remarkably tough shirt to wear. Play it too safe and you’ll end up looking like an accountant. Our suggestion: get adventurous.

This Native Son shirt does it just about perfectly, with oversized stripes to elevated it out of CPA territory into something a little bit riskier. The box pleat in the back and generally shrunken cut keep things slim, and the button-down collar means you’ll emerge with your preppy cred intact.

It’s the rare class of shirt you can wear under a suit or above a bathing suit, which should be a pretty useful trick once July rolls around.

—R.B.

CONTRIBUTORS

  • Russell Brandom