Timberlands that never once graced a construction site. Surf shorts that never saw a beach. Boat shoes that never set foot on a dock. The ’90s were, if nothing else, a perplexing time for fashion. From the ankle-bearing allure of capri pants to the ease of throwing your hair up with a brightly-colored scrunchie, you probably have some regrets. But at the time, some seriously ’90s fashion trends were only worn by the coolest of the cool. Read on for the definitive list of the phattest, flyest style moments from this defining decade, and don’t be surprise if you end up shopping vintage clothing on style when you’re done. For more from this multi-faceted era, check out The Biggest ’90s TV Teen Idols, Then and Now.
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