33. Hugo Boss
The film Wall Street took place in the '80s, but finance bros were still making cash hand over fist throughout the '90s. And any player worth his salt was caking in a Hugo Boss suit. The Hugo Boss suits of the '90s weren't as severe as the power-dressing Gordon Gekkos of the '80s, but the brand kept it chic as fuck with turtlenecks, sloped shoulders, and a breezy European vibe. Some shady Nazi business was brought up in the late '90s, which the brand awkwardly dealt with. But before this nasty past stuck in the back of everyone's minds, Hugo Boss was the brand of choice for Wall Street sharks.