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Ah, the Kentucky Derby—the day of the year when every man considers it his duty to drape himself in cloth and accessories befitting the Tom Wolfe or KFC’s “Colonel.” Now, we love a free pass to express our inner dandy as much as the next guy—the Derby is a great opportunity to break out those pieces you weren’t sure you’d ever have an occasion (or the guts) to wear. But we also believe Derby day shouldn’t be an excuse for Halloween’s half birthday. Here are a few tips on dressing for the occasion—without going over the top. —Desiree Browne
Nothing says "thank goodness winter’s over” like flowers. If you want to rock them without being too garish, shrink them down to size. The smaller the print, the more subtle and understated the look.
Shirt by Thomas Dean ($65)
Seersucker is such a Derby staple that it has slipped into something of a cliché. A good workaround to the full three-piece: Find an unusual and unexpected way to incorporate the textured cotton fabric into your wardrobe—say, a bow tie?
Tie by Paul Fredrick ($39.50)
If you change just one thing about your usual look for the Derby, make it the addition of a pair of easter egg-colored chinos. But skip the loud contrasting-color ribbon belt.
Chinos by J. Crew ($75)
Ladies go all out with their toppers for the races. The fellas shouldn’t feel left out, but they should show a little restraint. A straw panama? Sure. Old-timey boater? If you can pull it off, more power to you.
Hat by Goorin Bros. ($140)
No restraint needed here. There should be no empty pockets on Derby Day. However, we like a standard solid-color square fold over a paisley poof.
Pocket Square by Topman ($10)
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