On Monday evening, the Council of Fashion Designers of America crowned Ralph Lauren menswear designer of the year, his 12th win since the show’s inaugural ceremony in 1981, making him the most decorated designer in CFDA history. The council even has a tradition of creating awards in Lauren’s honor, as it did with the Fashion Legend Award in 2007 and the CFDA Members Salute in 2018.
At 87, Lauren is the consummate businessman of American fashion and still produces master-caliber collections that build on his brand’s established codes. In addition to his business acumen and keen tailoring sense, the designer remains more relevant than 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 clothing, from his deep and abiding love of Western wear to his knack for mixing Waspy blazers with rugged workwear and military pieces, has always been at the heart of everything he does. Here are some of her best looks from the last 50 years.
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