Photography by Joshua Scott
Cigar-chomping gamblers and crooked mobsters aren’t the only guys who revel in a day at the races -- the sport also serves as the backdrop for refined gatherings. My Fair Lady’s professor Henry Higgins debuts his guttersnipe-turned-lady protégé, Eliza Doolittle, to genteel society at England’s Ascot Racecourse. Stateside, the Kentucky Derby is known as much for being an homage to bygone Southern charms—think seersucker-clad fops sipping mint juleps (check out our recipe here) in the shade of their dates’ formidable hats -- as it is for its equestrian endeavors. Enjoying some time trackside is suitable behavior whether you’re a betting man, gentleman, or, even better, both.
Clockwise from top: yellow silk printed pocket square by Salvatore Ferragamo, $160; Air Colton spectator wingtip shoes by Cole Haan, $198; jacket by Joseph Abboud Collection, $495; Mad Men Collection check button-down shirt by Banana Republic, $79.50; Funk hat by Hermès, $530