Few decades have seen changes in fashion as exciting, and stirring, as in the ’90s. The decade marked a tonal shift from the 1980s, which were synonymous with glitz, shoulder pads and big hair, and into clothes that were more comfortable, understated and considered. Brands like Miu Miu and Calvin Klein pushed clean-lined approaches to style that did away with excess, while style icons like Carolyn Bessette-Kennedy confirmed the adage that less is often more, and just as impactful.
But that doesn’t mean everyone played it safe. In fact, it was the opposite, for more liberated attitudes gave way to greater amounts of fashion experimentation. There were the dresses made by red-carpet enfant terrible Gianni Versace, whose risqué aesthetic was embraced by existing and emerging superstars on the red carpet, or those who, like Sharon Stone and Chloë Sevigny, were unafraid to flip conventionality on its head. Keep reading for them stirring histories behind these 15 red-carpet looks from the ’90s, which turned heads and set trends for all different reasons.