Renowned for her aversion to skirts, Hepburn preferred pants, pioneering the tomboy chic style during an era when formal dresses were the norm
Epitomizing elegance and femininity in the 1950s, Grace Kelly's wardrobe reflected sophisticated glamour, even after becoming a princess
A symbol of allure with her platinum blonde hair and sultry dresses, Monroe's fashion legacy includes the iconic white pleated halter dress from "The Seven Year Itch
Former First Lady Jackie O’s style evolved from the iconic pink suit and pillbox hat to a signature look of head scarves and oversized shades in the late 60s and early 70s
A 60s socialite and muse to Andy Warhol, Sedgwick was known for her performance art style with leotards, leopard prints, and chandelier earrings
Famous for her super short pixie haircut in "Rosemary’s Baby," Farrow's style featured Peter Pan collar dresses and graphic prints
A mega-star from The Supremes, Ross embraced the flashy 70s with big hair and grand dresses, blending costume and everyday fashion
Known for embracing the gap in her front teeth as part of her look, Hutton epitomized classic American style with streamlined colorblock suits in the 70s
Influenced by menswear, Keaton's wardrobe in "Annie Hall" included wide ties and wide-leg trousers, defining her style for years
The Blondie frontwoman brought punk to glamour with thrift store finds and neon accents, becoming an icon in the late 70s and early 80s