No Doubt's Gwen Stefani came onto the mainstream music scene with the 1995 ska-punk album, Tragic Kingdom. Her laid-back California fashion sense was a mix of tomboy, skate-style outfits comprised of crop tops and low-slung pants.
While the early aughts brought on squeaky-clean pop stars, Karen O of the Yeah Yeah Yeahs served as the cooler, fearless alternative. Her experimental on-stage aesthetic was almost always in collaboration with artist-designer Christian Joy.
These leggings in a trippy tie-dye print would make a big style statement while allowing Karen O to move about on stage.
Annie Clark, aka St. Vincent, used fashion to transform from chill, indie Brooklynite to an experimental art-rock force of nature. Her 2017 album Masseduction was a prime example: colorful silhouettes and a lot of latex.