Save this story Save Story Save this story On 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.
Expand Arnaldo Magnani 1/17 2001 Technical 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.
Expand Dirck Halstead/Getty Images 2/17 1986 Like 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.
Expand Ron Galella, Ltd./Getty Images 3/17 1987 There’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.
Expand Clive Brunskill/Getty Images 4/17 2006 A 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.
Expand Randy Brooke 5/17 2007 Think a funky belt can’t be the defining element of an otherwise understated fit? Lauren would respectfully disagree.
Expand Fernanda Calfat/Getty Images 6/17 2008 Few 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.
Expand Penske Media/Getty Images 7/17 1989 Lauren 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.
Expand JP Yim/Getty Images 8/17 2015 Yacht club up top, honkey tonk downstairs. Another Lauren signature.
Expand Jack Robinson/Getty Images 9/17 1970 Ralph 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.
Expand Henry S. Dziekan III/Getty Images 10/17 2010 Style 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.
Expand WWD/Getty Images 11/17 1977 There’s perhaps no more challenging look to pull off than “office cowboy,” but Ralph Lauren makes it look easy.
Expand Victor VIRGILE/Getty Images 12/17 2001 Leather pants and a denim shirt under a tweed jacket is another decidedly advanced maneuver, but (if executed correctly) a potentially powerful one.
Expand Victor VIRGILE/Getty Images 13/17 2012 In recent decades, Lauren has increasingly swapped his signature cowboy boots for La Sportiva hikers, anointing gorpcore in the process.
Expand WWD/Getty Images 14/17 2014 Lauren 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.
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Source: Celebrities
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