Courtney Love and Kurt Cobain (1991)
The king and queen of Seattle grunge, Kurt and Courtney are arguably the most influential couple in 1990s fashion. The Hole frontwoman was known for her torn, sheer slips, dark makeup, and babydoll dresses, and is credited for popularizing the "kinderwhore" look that had a moment in the early '90s. Similarly, the Nirvana singer arguably started the entire grunge trend, with his mismatched, oversized outfits and shaggy mop of hair. We can't think of anyone in history who could make a flannel look so good, and with so little effort.