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The Most Stylish Fashion Designers of All Time

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The Most Stylish Fashion Designers of All Time

Sure, the clothes they create are iconic, but what about the stuff that Hedi Slimane and Tom Ford actually wear? And how do young guns like Riccardo Tisci and Marc Jacobs stack up against godheads like Ralph Lauren and Giorgio Armani? This is our ironclad list of the best-dressed men in menswear—and what you can learn from them

Modest Look, Mad Lifestyle Halston His signature piece would become a serious-looking black turtleneck. By day, he wore it to dress Jackie O and Liza Minnelli. By night, he wore it while garnering a rep as one of the most excessive partyers in an excessive era at the most excessive of locales: Studio 54. (And for the record: His first name was Roy, but everyone just calls him Halston.) Photo: Jean Barthet

American Royal Ralph Lauren The first 360-degree lifestyle brand and one of the biggest fashion empires in the world, all based on one man’s closet. Each of Ralph’s personas is a romantic American archetype: He’s the boardroom kingpin, the East Coast preppy, and the Wild West rancher rolled into one. And the clothes he sells are the clothes he needs to live out that fantasy. Except that for Ralph—thanks to the sheer force of his vision, his talent, and his will—it’s not a fantasy at all. Photo: Leslie Goldberg

The Man, Not the Monogram Yves Saint Laurent He was real, and he always dressed for the occasion: a white lab coat in the atelier, dark suits at a party, structured safari jackets for the urban jungle. And always the specs—those big plastic frames—remained front and center. Photo: Unknown

The Craftsmen Hubert de Givenchy Hubert de Givenchy’s elegant clothes turned Audrey Hepburn into a style icon but the designer’s own restrained uniform—dark suit, crisp white shirt, dark tie—is what holds up for us today. de Givenchy consistently moved fashion’s needle forward via cutting edge techniques but always knew the best way to make any design successful was to make it timeless. Photo: John Chillingworth/Picture Post/Hulton Archive/Getty Images

Bad Boy Marc Jacobs Before the eight-pack abs and the mega-empire, Jacobs was a brooding young gun with long hair, grungy clothes, and a grungier attitude. Throughout his transformations, the looks have changed, but the same rebel spirit remains. Photo: Steven Klein

The Thin White Dude Hedi Slimane of Saint Laurent As both a designer and a photographer, Hedi Slimane has always been drawn to the street urchin, the gutter punk, the whippet-thin rock star. Those looks describe his personal style, too: drainpipe jeans, a second-skin leather jacket, and a tie that (like Slimane) seems to have been on a crash diet. He’s easily mistaken for one of his subjects—and that’s just how he likes it. Photo: Nan Goldin

First Class Bill Blass Blass was American fashion’s consummate gentleman and always dressed the part. A former army man from the Midwest, his well-tailored civvies—suits and checked blazers at the office, a tuxedo after six—put him in lock step with high society, which just so happened to be chock full of the women and men who couldn’t get enough of his clothes. Photo: Glen Martin/The Denver Post via Getty Images

A Man in Uniform Thom Browne His shrunken gray flannel suit is “repressed 1950s American businessman” taken to cartoonish (some might say fetishistic) extremes. He started wearing it religiously, and people began to take notice. First it launched his career; eventually it changed the look of modern suiting. (No exaggeration.) Photo: Courtesy of Thomas Iannaccone/Condé Nast Archive

The Figurehead Karl Lagerfeld of Chanel You know him now for his emblematic style—that white-ponytail-and-gangster-shades silhouette has a Q rating as high as the Bat Signal. But even back when Lagerfeld took over Chanel, perma-clad in a jacket and tie that he wore like a suit of armor, he understood the power of both designing for a brand and being one. Photo: Courtesy of Thomas Iannaccone/Condé Nast Archive

Glitz is Good Gianni Versace You could concoct a name for Versace’s singular style: Gleaming aristocrat-playboy? Silken rococo cowboy? But it’s so much easier to point at the high-flying lifestyle he created and just say: that. Photo: Richard Young/Rex USA

The Maestro Giorgio Armani He set men free from the confines of their own suits. First, he took a scalpel to his own jacket, leaving just the essentials: Armani scrapped the shoulder pads and switched to softer fabrics. (See: Richard Gere preening in American Gigolo to get the idea.) He’s since adopted blue T-shirts (and at 80 years old, the guy still has a crazy-taut physique underneath), but the idea remains the same: A man’s clothes serve him best when he’s comfortable wearing them.

Handsome Devil Riccardo Tisci of Givenchy He’s an Italian designer at a French house with a psychic link to the U.S. streets. All respect to Jay, Ye, and the NBA, but no one wears Tisci’s designs—from tuxes to graphic tees—with as much “fuck you” as the man himself. Photo: Stephane Feugere

Living the Brand Calvin Klein He practically invented the tee-under-a-suit look that the rest of us are all wearing now more than ever. Before Kate and Marky Mark, Klein was his own brand ambassador and proved that all-American style doesn’t have to be nostalgic—it can be forward thinking and modern. Also, he’s always had really good hair. Photo: Ron Galella/WireImage/Getty Images

Italian Stallions Domenico Dolce & Stefano Gabbana Behind the scenes, Stefano (the tall one) brings the inspiration and energy while Domenico brings the expert tailoring and craftsmanship. But in public, the two present a united front: white dress shirts and skinny ties at their shows, tank tops and tiny swimsuits while sunning on vacation with supermodels. Photo: Simon Watson/Trunk Archive

The Roman Emperor Valentino Garavani He’s designed for some of the world’s most famous men (and pretty much every famous woman), but if you want a case study in how to dress for the good life, look no further than the perennially tan Valentino. These days, Garavani’s impeccably tailored suits with colorful silk pocket squares have him dressing like high fashion’s elegant elder statesman (which he is) as he jets between chateaus around the globe. Photo: Gianni Giansanti/Sygma/Corbis

Leading Man Tom Ford He’s not so much a man as The Man, a self-made archetype of what masculinity could be if we all tried a bit harder and elevated our taste a level (or seven). From the impeccable black suit to the flawless stubble to his intense disdain for the top five buttons on a dress shirt, he makes looking godlike seem way easier than it actually is. Photo: Simon Perry

 

 

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