When: 1990 

One of the things you can jack from your dad are the windbreakers that he would unrelentingly rock in the '90s. Bruce Jenner, being the vintage bro that he is, had the style on lock. Dude stayed flexing while looking like he was always fresh off the track. This look is so easy and comfortable, and the bright colors that the '90s has always repped make the style's archives just as great today as they were back then.