1. How to Marry a Millionaire (1953)
If there's anything more stylish than a Marilyn Monroe movie, it's a Marilyn Monroe movie that co-stars Lauren Bacall and Betty Grable. The powerhouse trio is impossibly chic throughout this film. Plus, Monroe makes a reference to a character being in Harper's Bazaar three times as an indicator of her class, so you know it must be good.
2. High Society (1956)
Grace Kelly delivers her signature ice queen style in this classic film with Frank Sinatra and Bing Crosby. Whether she's owning the night in a sweeping evening gown or lounging poolside in a retro white one-piece, Kelly is every bit the princess.
3. Charade (1963)
While Funny Face and Breakfast at Tiffany's may be the Audrey Hepburn films most commonly associated with high style, Charade is not to be missed. Hepburn stars alongside the dashing Cary Grant in this mystery thriller, dressed in 60s-era car coats, shift dresses, kitten heels, and oversized sunglasses. Not to mention the hat collection of your dreams.
4. Valley of the Dolls (1967)
Despite its unsettling plot, Valley of the Dolls still captures the chic glamour of the mid-'60s in New York City.
5. Barbarella (1968)
As the sexy title character in this campy cult classic, Jane Fonda employs a killer pair of space-age boots to save the galaxy from the villainous Durand Durand.