Though his trainer, Patrick Kelly, had thought to take Evening Attire out of stakes competition, NYRA stakes coordinator Andrew Byrnes convinced him to enter the horse in the June 6, 2008, Brooklyn Handicap at Belmont Park contested at a mile and a half. With Cornelio Velásquez aboard, ten-year-old Evening Attire placed, coming from sixteen lengths behind at the quarter pole and going down the center of the track to rapidly close on five-year-old Delosvientos. Delosvientos went wire to wire, but the slowly breaking Evening Attire got within two lengths of the winner. Patrick Kelly said, "In the barn today, he had his game face on early. I’m always happy when he's in the money. It was fun to try."