#24: Nancy Sinatra
Nancy Sinatra defined cool, mod-era pop in the 1960s with hits like “These Boots Are Made for Walkin’,” “Sugar Town,” and her Bond-worthy duet “Somethin’ Stupid” with Frank Sinatra. Blonde, sharp, and effortlessly stylish, she turned pop music into a fashion statement and a mood.

Her life mixed legacy with reinvention. As Frank Sinatra’s daughter, she initially struggled to escape his shadow, but total image reinvention changed everything. Close to the LA music scene, she dated musicians, worked with Lee Hazlewood, and carved out independence with confidence, wit, and a very knowing wink.
