Geena Davis in Thelma & Louise
PACKING ESSENTIALS: Opt for casual tees that feel a little bit rebellious and a lot rock ’n’ roll—and pair them with nostalgic acid-wash denim you’ll share with your ride or die.
Textile headband ($12, simons.ca)
Re/Done cotton T-shirt ($150, saksfifthavenue.com)
Denim jeans ($67, topshop.com)
Brave leather belt ($105, braveleather.com)
Baby Spice circa Spice World
PACKING ESSENTIALS: More than 20 years later, pumped-up platform kicks still slay when worn with a strappy slip dress—even if you’re not planning on travelling on a luxe double-decker bus.
Theodora Warre gold-plated-sterling-silver necklace ($301, matchesfashion.com)
Birks silver and enamel earrings ($175, maisonbirks.com)
Miss Selfridge slip dress ($55, missselfridge.com)
Naked Wolfe leather and suede sneakers ($364, nakedwolfe.com)
Wesley Snipes in To Wong Foo, Thanks for Everything! Julie Newmar
PACKING ESSENTIALS: Glam meets camp meets old-world Southern whimsy in this something-for-everyone spin on covetable warm-weather style.
Cara headband ($36.69, nordstrom.com)
Floral print blouse ($49.90, zara.com)
Floral printed flared pants ($49.90, zara.com)
Catbird 14-karat-white-gold and diamond earrings ($535, catbirdnyc.com)