Band: Nirvana

This man dressed most the '90s. Many of the trends we remember-flannel shirts, ripped jeans, oversized sweaters, were often seen on this guy—and believe it or not, they still hold up today. While he may not have started them, he definitely made them iconic. From appearances on MTV Unplugged in an oatmeal-colored cardigan, to the Daniel Johnston T-shirts that helped catapult the latter into popularity, Kurt was an unwilling trendsetter. His slovenly style and appearance may have represented his disregard for societal norms, so it's ironic that they came represent the zeitgeist of a decade.