Evening Attire made his first start on July 16, 2000 in a maiden special weight race at Belmont Park, finishing second. He broke his maiden in his next start at Saratoga on August 6. He then stepped up in class to enter the Grade I Hopeful Stakes at Saratoga on September 2 but finished seventh. He then lost five straight races in allowance company in a 13-month span, during which time he was gelded. He finally returned to the winner's circle on October 31, 2001 in the Discovery Handicap, then followed up with a win in the Queen's County Handicap.