34. Boyz II Men
Why They Made The Cut: Remember when they rocked Jordans to the Grammys?
Okay, we have to admit: Grown-ass men dressed like themed quadruplets is pretty lame in retrospect. But at the time it was fire. From actually making sweater vests look good to their coordinated suit ensembles, their style legacy was established when they all rocked Jordan 11s with tuxedos-people went nuts!