Leonardo DiCaprio's Most Stylish Roles

Ranking the characters whose style killed it.

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Complex Original

Image via Complex Original

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Leonardo DiCaprio has a history of picking out some well-dressed roles. From men like Howard Hughes in The Aviator to his turn as "Jay Gatsby" in The Great Gatsby, he's played some parts that require some serious dressing up. Being the avid cinephiles that we are, we sifted through his oeuvre (including obscure flicks like Don's Plum and The Foot Shooting Party, you film snobs) to find the parts with the freshest kits. And then we ranked them, because we're crazy. So sit back (consider pouring a stiff drink to get in the mood) and take a look through Leonardo DiCaprio's Most Stylish Roles.

25. Richard

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24. William "Billy" Costigan Jr.

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23. Hank

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22. Brandon Darrow

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21. Arnie Grape

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20. Jim Carroll

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19. Teddy Daniels

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18. Josh

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17. Roger Ferris

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16. Dominic Cobb

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15. Calvin J. Candie

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14. Frank Wheeler

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13. King Louis XIV/Philippe

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12. Amsterdam Vallon

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11. Fee "The Kid" Herod

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10. Arthur Rimbaud

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9. Jack Dawson

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8. J. Edgar Hoover

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7. Tobias "Toby" Wolff

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6. Jordan Belfort

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5. Romeo Montague

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4. Howard Hughes

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3. Jay Gatsby

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2. Frank William Abagnale Jr.

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