Churchill Downs Duds: The Best Kentucky Derby Men’s Outfits of 2021

One of the best things about The Kentucky Derby (aside from the day drinking and the possibility of winning some cash on a preposterous bet) is the fact that it comes on the first Saturday in May every year, rain or shine. This means, for the sartorially minded gentleman, there’s a whole year of deliberation to get your Derby look just right.

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This year (like many in the recent past), it rained at Churchill Downs, and all those pre-planned pastels, pinstripes, seersucker, and linen suits were either covered in plastic ponchos or soaked through (mad props to the gentleman below for his clear plastic poncho, allowing for his perfect Derby suit to still be visible). Top that off with the controversy over which horse actually won – Maximum Security lost due to a disqualification, leaving the winner’s circle open for the delightfully named Country House – and you’ve got a race for the ages.

So, forget the dispute for a little while and focus on things a little more sartorial. Here are the best men’s outfits from Kentucky Derby 2019, featuring an assortment of suiting styles and accessories. Let these guys be your guide for next year’s Derby duds.

The Best Men’s Looks from the 145th Kentucky Derby

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Kevin Richardson of Backstreet Boys fame brought it with this perfect Derby look. Cream pants contrast with a deep, dark blue blazer, a gray vest, blue and white-striped shirt (with matching pocket square) and tie. Topping it off is the quintessential derby hat.

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The 70s were strong with Wilmer Valderrama on Derby day with this style swerve. A tan-gray suit (with pleated pants!) is offset with a light, white shirt with floral pattern. The dark shades and dark shoes pair perfectly with one of the more sedate outfits we saw at the 145th Kentucky Derby.

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David Allen Grier turned up in a blue-gray, subtly-patterned suit, a tiny cheque pink print shirt, and coordinating magenta and purple tie. Like many men at the 2019 race, he also capped off his look with a derby hat.

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Tom Brady went with a classic striped shirt, khaki, and pocket square, only he opted for black rather than a classic Derby pastel. Jimmy Garoppolo, on the other hand, opted for a pale pink shirt with pink madras print blazer.

Hopefully Louisville rapper, Jack Harlow, won’t be making any circuits around the infield, because white and mud do not mix. But we love the bombast of this white suit and blood-red shirt and tie, reminiscent of the Derby’s white and red color scheme.

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Blue suede shoes and a blue blazer with matching checkered tie, with complimentary yellow hat makes former football player Warren Moon’s outfit one of the simplest, though stylish, that we saw.

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Professional Lacrosse player, Paul Rabil passed on the derby hat and opted for a fedor instead. Standing in a pair of gray suede boots (with patterned socks), a blue and black patterned suit, plain white shirt, and blue tie with money clip, Rabil looks the classic derby part … until you get to his orange belt – which is the simple pop of color that derby style aficionados swoon over.

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While Justin Sutherland nailed his derby outfit by going pink, pastel, and bow-tied beautiful, chef Pablo Lamon went a little too formal and stuffy for this occasion. Lamon’s black lapel-ed maroon jacket and black bow-tie are too somber for this more light-color oriented event.

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Bode Miller slides through the crowds in one of the boxes at the 145th Kentucky Derby. His blue windowpane checkered suit, paired with a pale pink tie and shirt blend in with the rest of the crowd, while still sticking out (in a good way).

If you need some additional Kentucky Derby men’s outfit inspiration, check out this guide to seersucker and you’ll be prepped and ready come Derby Day ’20.

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