$895
billyreid.com

Designer Reid, now 42, opened his first clothing company in 2000 and received glowing write-ups in GQ and Vogue. He won the prestigious Perry Ellis Award for Men's Wear in June 2001, but following his Sept. 10 runway show, the aftermath of 9/11 cut so deeply into his revenue that he had to fold the business. In 2004, backed by retail entrepreneurs, Reid launched a new company, based in Florence, Ala. The fall line includes this water-resistant bag made of napa leather, a very soft calfskin.