When: 1990 

We're all for rocking the lightwash denim and that are affectionately referred to as "dad jeans," but this doesn't mean you should rock them like your dad did when he took you to tee-ball practice. Jenner's stonewashed jeans are nearly waist high and remind us of what Jerry Seinfeld used to wear. Hey, at least he gets the whole sneaker with jeans and button-up shirt thing. Shout out to Kris Jenner for working the OG street goth look.