- Jackie O’s Pillbox
Jacqueline Bouvier Kennedy famously paired a wool, double-breasted pink Chanel suit with a matching pink pillbox on November 22, 1963 — the day her husband was assassinated. The heartbroken style icon insisted on wearing the same, though now blood-stained, ensemble during Lyndon B. Johnson’s swearing-in ceremony.
- Audrey Hepburn’s Big Brim
Although Hepburn played many roles that emphasized haute hats, it’s Holly Golightly’s black, wide brim hat in “Breakfast at Tiffany’s” that has its own special place in the history of women’s hats.
- Diane Keaton’s Bowler
Famous for her daring delves into menswear fashion, Diane Keaton is a true hat icon. Wearing the now-famous black bowler hat as Annie Hall (a role written specifically for Keaton herself) in the 1977 Woody Allen hit, solidified the star’s androgynous fashion profile forevermore.
- Annie Oakley’s Cowgirl
The Annie Oakley cowgirl hat has long been regarded as a symbol of adventure, persistence and the Wild West. Trailblazers love the style so much that an authentic Annie Oakley Stetson hat sold for over $17,000 at a recent auction.
- Queen Elizabeth II’s Medium Brims
You can’t talk about hat icons without mentioning Her Majesty herself. All of the Queen’s structured, brimmed hats will have their place in history, but her sunny yellow Royal Wedding hat will forever have its place in the canon of women’s fashion.
