Ralph Lauren’s 17 Best Outfits of All Time

Skip to main contentRalph Lauren, the consummate businessman of American fashion, is now the winningest designer in CFDA history. But his most enduring contribution to menswear might be his own personal style.JON LEVY/Getty ImagesOn Monday night, the Council of Fashion Designers of America crowned Ralph Lauren as its menswear designer of the year—his 12th win since the show’s inaugural ceremony in 1981, minting him as the most decorated designer in CFDA history. The council even has a tradition of creating awards in Lauren’s honor, as they did with the Fashion Legend Award in 2007 and the CFDA Members Salute in 2018.At age 87, Lauren is the consummate businessman of American fashion, and he’s still producing masterclass-caliber collections that build upon his label’s established codes. In addition to his business savvy and keen eye for tailoring, the designer remains as relevant as ever in 2026 because of something far more ineffable: a deep-rooted sense of personal style. For Lauren, clothes aren’t just a wardrobe; they are identity. His own relationship with getting dressed, from his deep and abiding love of Westernwear to his knack for blending Waspy blazers with rugged workwear and military pieces, has always been at the core of everything he does. Here are some of his best looks from the last 50 years.Which looks were your favorite? Cast your vote.ExpandArnaldo Magnani2001Technical hiking gear was a relatively late addition to the RL oeuvre, but the man was wearing hikers in the city long before hipsters discovered Salomons.Is this your favorite look?ExpandDirck Halstead/Getty Images1986Like a skilled party DJ, Ralph Lauren has an uncanny knack for combining unlikely elements—like a yachtsman’s sweater and a pair of worn-in blue jeans—with complete ease.Is this your favorite look?ExpandRon Galella, Ltd./Getty Images1987There’s black-tie, and then there’s RL black-tie. There’s no doubt that Lauren can wear a pair of tuxedo pants and patent leather shoes as well as anyone, but he is much more himself in jeans and cowboy boots.Is this your favorite look?ExpandClive Brunskill/Getty Images2006A two-year stint at Baruch College in Manhattan was the closest Lauren came to the Ivy League, but that didn’t stop him from adopting repp ties, Oxford collar shirts, and other hallmarks of the East Coast elite. The juxtaposition of oversized aviator shades with this solidly trad look is quintessential Ralph.Is this your favorite look?ExpandRandy Brooke2007Think a funky belt can’t be the defining element of an otherwise understated fit? Lauren would respectfully disagree.Is this your favorite look?ExpandFernanda Calfat/Getty Images2008Few people will ever look as good in a biker jacket as Ralph Lauren did at age 70. The difference is in the details—the flannel shirt unbuttoned and tucked, the crisp white henley—and the confidence.Is this your favorite look?ExpandPenske Media/Getty Images1989Lauren is a master editor, but the magic of his greatest looks is in details like a vest tucked into trousers, a knotted belt, and a pair of precisely rolled sleeves.Is this your favorite look?ExpandJP Yim/Getty Images2015Yacht club up top, honkey tonk downstairs. Another Lauren signature.Is this your favorite look?ExpandJack Robinson/Getty Images1970Ralph Lauren never learned how to sew, but he has an instinctive understanding of tailoring. By blending the stiff silhouettes of Savile Row with the breezy swagger of American ivy style, he created a look that was all his own.Is this your favorite look?ExpandHenry S. Dziekan III/Getty Images2010Style is all about understanding the rules before you can break them. Lauren certainly does, and that’s why this ensemble—from the wide-spread collar and slim tie combination to the double-down on stripes—works as well as it does.Is this your favorite look?ExpandWWD/Getty Images1977There’s perhaps no more challenging look to pull off than “office cowboy,” but Ralph Lauren makes it look easy.Is this your favorite look?ExpandVictor VIRGILE/Getty Images2001Leather pants and a denim shirt under a tweed jacket is another decidedly advanced maneuver, but (if executed correctly) a potentially powerful one.Is this your favorite look?ExpandVictor VIRGILE/Getty Images2012In recent decades, Lauren has increasingly swapped his signature cowboy boots for La Sportiva hikers, anointing gorpcore in the process.Is this your favorite look?ExpandWWD/Getty Images2014Lauren has always revered the look of traditional British tailoring, from safari suits to Savile Row, but he’s just as likely to pair his flannel suits with cashmere turtlenecks and cowboy boots as neckties and Oxfords.Is this your favorite look?Sign up for Show Notes to get news on the latest runway shows, parties, and insider events on the international fashion circuit.Jeremy Freed writes about style, culture, and watches for GQ. His work also appears in Puck, The Globe and Mail, and The Wall Street Journal, among other fine publications. His favorite sandwich is the #19 at Langer’s. Jeremy is the author of American Style: The Look and Legacy of John ... Read More