Diddy and his girlfriend Cassie Ventura chose matching leather looks to celebrate Usher’s 35th birthday in LA on Monday night. It may have been nighttime but that didn’t stop Diddy from donning a pair of sunglasses as he left West Hollywood. Cassie’s white sweater and baggy leather pants were decidedly casual, she spiced up her outfit with heels and a hint of cleavage. See their matching fits below!