When: 1982

Kanye West said his mink was dragging on the floor, and while Jenner didn't have a drapey fur, his shearling bomber jacket denoted that he was the fucking man. Sure, this isn't a jacket you'd see worn by fighter pilots during WWII. But it's so exagerrated and ridiculous, we can't help but think Jenner was welcomed by the ladies the same as a war veteran who returned home in a similar garment.