The Kentucky Derby is not just about horse racing—it’s a fashion event where classic Southern style meets bold, sophisticated looks. Men’s attire typically blends traditional elegance with playful Derby flair. What to Wear: Kentucky Derby Attire Male 2025? While the Derby encourages creativity, the general rule is "Dress to Impress"—think upscale Southern charm with a touch of playful sophistication. Whether you go classic or trendy, comfort and style should go hand in hand.