Jockey Club Gold Cup
In 2002, he earned his most important win in the Jockey Club Gold Cup. That year, he also won the Aqueduct Handicap, Saratoga Breeders' Cup Handicap and Red Smith Handicap while also finishing fourth in the Breeders' Cup Classic. In 2003, Evening Attire earned only two allowance race wins but was second in both the Clark and Queens County Handicap and was third in both the Whitney and Jockey Club Gold Cup.