When: 1993

The beach is made for catching rays, chugging 'Ronas, and living the wild, single life. We imagine this is something Jenner is doing these days, but back in the '90s he was posted with his boo-thang, Kris, and rocking out in T-shirt he scored from a volleyball invitational. '90s gear was dope because it was over-branded, but Jenner keeps it simple, and looks ready for a day of slaying rum buckets and chowing down on mahi-mahi tacos.