When: 1977

Bellbottoms are a trend that we hope never comes back. Jenner, unfortunately, fell victim to the flare-leg swagger of the '70s, but his striped longsleeve T-shirt distracts from the mushrooming inseam of his trousers. While pant fits come in and out of style, striped shirts will always be awesome, even if you're a dude who's learning how to figure skate.