5. Calvin Klein
From OJ to Bill Clinton, the '90s was a decade that adored controversy. There was no other clothing brand that stirred up as much controversial trouble as Calvin Klein. From plastering incredibly homoerotic imagery on high-exposure billboard to creating the "heroin chic" aesthetic that Bill Clinton called "deplorable," Calvin Klein's brand pissed off all of mainstream America while giving stylish dudes the opportunity to dress in European-esque minimalist clothes that were as chic as they were masculine.