Churchill Downs Duds: The Best Kentucky Derby Men’s Outfits of 2019

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.

best kentucky derby mens outfits man in rain poncho stands with straw hat
Jeffrey Brown/Icon Sportswire via Getty Images

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

best kentucky derby mens outfits kevin richardson and wife kristin
Jeffrey Brown/Icon Sportswire via Getty Images

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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