Peter O’Toole, Guy Pearce, and Jude Law have each tried their hand at portraying this larger-than-life Australian actor on the big screen, but none have fully captured Errol Flynn’s swashbuckling swagger and debonair style.
Flynn may be most famous for the sword-fighting heroes he played in films and the laundry list of scandals in his personal life (he even titled his autobiography My Wicked, Wicked Ways), but he also deserves recognition for the influence his sense of style has left on the generations of leading men who followed in his footsteps.
Flynn was a fashion chameleon. He epitomized the luxurious, extravagant lifestyle he lived off-screen with smart suits and patterned ties, and became the embodiment of rugged machismo in the roles he played on-screen. He even made Seinfeld-style puffy shirts look cool.
What may have come to define his style more than anything, though, were his grooming habits. He sported a hairstyle of controlled waves that was one of the most popular looks of the 1930s, and a pencil mustache that has now become synonymous with his suave and caddish ways.
And we can’t forget his most lasting contribution to popular culture: the phrase “in like Flynn,” which refers to his unparalleled prowess with the ladies.