Your forefathers knew a thing or two about style. From a well-fitting suit to a leather jacket, the legwork for refining a timeless look has already been done for you. Read on as our deconstruction of the most classically stylish dudes—and the pieces you'll need to copy them—continues.
Peter ToshHow could one of the trailblazers of reggae (and original member of Marley's Wailers) not be included among the classic style icons? Peter Tosh couldn't have been uncool if he tried—and that, of course, was reflected in his wardrobe. Tosh just about always rocked a hat or beanie; our favorite iteration comes with some military flavor. Tosh proves an army jacket with a pair of jeans is timelessly stylish. 511 Slim Fit jeans in neue grey, Levis; Peter Tosh Legalize It T-shirt, Worn Free; Tropic Monty beret in putty, Kangol; Pea Coat With Binding in chive, John Varvatos; vintage infantry pin, Etsy; black suede Chuck Taylor Double Zip High Top, John Varvatos for Converse.
Marlon BrandoIf you're thinking Marlon Brando's look here was a lot like James Dean's, you're right. Dean copied Brando, right down to the white tee. And can you blame him? Brando made the undershirt an outer-shirt, boldly wore jeans to fancy events (very much a faux pas in those days) and exuded "rebel with a heart of gold" like no other. A plain white T-shirt and a leather jacket are two absolute must-haves for any man's closet. Ishida Leather Biker Jacket in indigo, All Saints; The Essential Crewneck T in optic white, Gap; 1955 501 Jean in rough rinse, Levi's Vintage Clothing; Rogan Engineer boot in dark brown, The Frye Company; Fuse Belt in bark, All Saints.
Peter BeardTake away Peter Beard's blue blood pedigree and life among Amazonian models, and you would still have one stylish dude. Beard's years as a swashbuckling photographer in Africa made him down-to-earth and, inadvertently, the father of "safari chic" in the U.S. The sense of daring that fueled his work didn't stop when Beard was off-duty; he was brave enough to sport his signature sandals (seen in the spread above) and traditional African sarong on the streets of Manhattan. A guy who can wear what is basically a skirt without blinking an eye deserves his status in the style history books. Selvage Madras Solid E-Z Fit, Gant Rugger; M Typ 240 camera, Leica; Belted Field Jacket, Belstaff; Men's Federale Jacket in alpha green, Patagonia; traditional Kenyan kikoy, special order; Leather Sandals, Beam Plus Horween; Men's Duck Pants in retro khaki, Patagonia.
Michael CaineWith that cockney accent he refused to shed, Michael Caine never let his stardom compromise who he was and where he came from. Though Caine was partly so well-dressed due to a contractual agreement that he could keep his character's wardrobe from every film (smart guy), he clearly knew what looked good. A slim-fitting suit, cufflinks and a classic pair of shades. Collection 54mm Sunglasses in espresso, John Varvatos; One-button suit in grey, Emporio Armani; Ward Plain Shirt Double Cuff in pink, Thomas Pink; Narrow Black Jacquard Stripe Tie, Paul Smith; Michael Caine Glasses Cufflinks, Paul Smith; Black Falconer Chelsea Boots, Paul Smith.