1. Willy Wonka’s Top Hat – ‘Willy Wonka and the Chocolate Factory’ (1971)
The on-screen charisma of Willy Wonka comes largely from Gene Wilder’s masterful performance, but we also have to give due credit to the costume department. Wonka’s tall brown top hat sticks out in every shot and perfectly embodies the character’s eccentricity. It’s the exact hat you’d imagine a flamboyant chocolate factory owner would wear.
Johnny Depp’s purple top hat in “Charlie and the Chocolate Factory” (2005) doesn’t have the same lasting appeal. But don’t feel too bad for Depp, because he makes another appearance later in the list.
2. Alex DeLarge’s Derby – ‘A Clockwork Orange’ (1971)
One of the greatest and most disturbing films of all time also features one of the most iconic cinema hats. The derby is usually reserved for high-status dress codes, making it feel more out of place on the head of sadistic main character Alex DeLarge. He does most of his dirty work while wearing the derby, and his crew of miscreants also wear various black top hats.
3. Jake and Elwood’s Fedoras – ‘The Blues Brothers’ (1980)
The fedora has made many appearances in cinema, but Jake and Elwood Blues are the most iconic duo to wear the hat. It fits perfectly with the brothers’ laid-back personalities and on-stage antics throughout the film. It’s hard to imagine this movie doing as well as it did without the main characters’ memorable costumes.
4. Indiana Jones’ Outback Hat – ‘Indiana Jones’ Franchise
Legendary big screen hero Indiana Jones wears the same dusty outback hat in all four films, from “Raiders of the Lost Ark” (1981) to “Kingdom of the Crystal Skull” (2008). The hat is so synonymous with Jones’s character that most people simply call it the “Indiana Jones hat” and ignore its real name. The outback hat remains a well-known pop culture clothing item thanks to Jones’ lasting legacy.
5. Captain Jack Sparrow’s Tricorn Hat – ‘Pirates of the Caribbean’ Franchise
Johnny Depp gets his due credit here with Captain Jack Sparrow’s tricorn hat. This hat was a common accessory for men in the American Colonial times, but nobody rocks it quite like Sparrow. He has a humorous relationship with the hat throughout the films, always losing and retrieving it in slapstick ways.
6. Sherlock Holmes’s Deerstalker Cap – ‘Sherlock Holmes’ Franchise
Sherlock Holmes’s most memorable character trait is his profound wit, but his deerstalker cap is a close second. No other noteworthy character in modern cinema has been able to pull off this hat style, but Holmes does it with ease. The phenomenon isn’t limited to one actor, either. Sir Ian McKellen, Robert Downey Jr., Peter Cushing, and all the others wear it with the same grace.
7. Daisy’s Hats – ‘The Great Gatsby’ (1974)
“The Great Gatsby” is full of extravagant clothing, but Daisy’s hat collection always seems to stand out. She wears many hats throughout the film, with each one capturing the gilded romanticism of 1920s New York in its own unique way. Her hats in the 2013 rendition of the story are also memorable, but nothing beats Mia Farrow’s original performance.
8. Bonnie’s Beret – ‘Bonnie and Clyde’ (1967)
Faye Dunaway’s Bonnie is the polar opposite of Mia Farrow’s Daisy, but they find themselves on the same list thanks to their memorable headwear. Bonnie’s French beret became a counterculture statement from the moment the film hit the big screen and remains a powerful symbol of liberation to this day, for reasons good and bad.
9. Gandalf’s Hat – ‘The Lord of the Rings’ Franchise
Film critics consistently rank Gandalf among the best film characters of all time, and yet the wizard’s pointy gray hat remains his greatest defining feature. In a world with dark lords, elves and dwarves, it’s funny to see a powerful figure like Gandalf walking around in such an odd, oversized hat.
10. Oddjob’s Bowler – ‘Goldfinger’ (1964)
The final spot goes to the henchman Oddjob’s bowler hat — the only hat used to decapitate someone in cinema history. The brim of the bowler has sharp blades and is one of Oddjob’s many hidden gadgets in the film. Few henchmen have managed to leave a lasting impression in the Bond franchise, but Oddjob is certainly one of them, thanks to his weaponized hat.
Hats Make Things Interesting
This list covered a wide variety of movie characters, which goes to show how versatile and appealing hats can be. They have a knack for making things interesting, no matter their context. Try one of these iconic movie hats on for size and see what happens.
