For the track fashion set, it was the event of the season. Both the well-heeled locals and the A-list out-of-towner racing world crowd filled the (where else?) National Museum of Racing and Hall of Fame, a meticulously accessorized sea of dresses, fascinators and hats vying for a good seat for the much-anticipated Miss Scarlett fashion show. All were in good spirits thanks to the morning’s less-than-stingy pours of rosé and sparkling wine.
And at the center of it all, in a dapper white seersucker suit for the blisteringly hot summer day, was fashion icon Carson Kressley. “I just love the history and style of Saratoga,” he says. “Everyone looks so great.”
It was, frankly, about time Kressley hosted a big event during Saratoga’s meet. A life-long horse enthusiast who loves telling the story of “conning” his parents into taking him to Saratoga Race Course as a teenager (when looking at colleges, he told them he had to visit Skidmore—in August), he’s judged the Longines Prize for Elegance fashion competition at the Breeders’ Cup and made the rounds to Preakness, the Kentucky Derby and other huge horse events. “Every time I go to Saratoga, it gets better,” he says. His first full day at the track without his parents was back in 2005. “It was just as magical, special, unique, old-fashioned and wonderful as I’d remembered it.”
Kressley grew up on his family’s farm outside of rural Allentown, PA but gracefully made his way to the bright lights of NYC to forge a career in high fashion. “Where I grew up was not a particularly glamorous area, but the ’70s were a glamorous era where people were having parties at home,” he says. “I would watch my mom dress for them; my love affair with clothes started with her.” Always “captivated” by his mother’s glamorous hostess skirts and Bob Mackie–esque, Carol Burnett–worthy dresses, he developed a knack for fashion and as a young adult started to work his way up at Ralph Lauren, eventually landing in the label’s legendary advertising department. But he was soon to discover that his destiny wasn’t nestled solely among the upper crust—he was born to bring fashion to the masses. After an on-a-whim audition won him a role on TV’s Queer Eye for the Straight Guy, it was a rapid rise from behind-the-scenes work with supermodels to being thrust in the limelight himself. “We shot the pilot in Austin in 2002, and it first aired in July of 2003,” he says. “The next week we were on Ellen and The Tonight Show. It was a bit of an overnight sensation.”
Indeed—and with good reason.
The rise of the “metrosexual” male had created a boom of men’s grooming products and more refined fashion pieces, but there was little out there to help them navigate it all. And the workplace wasn’t the only area demanding a man level up his look—women were more than ready to kiss the era of flannels and baggy jeans good-bye. Magazines such as GQ and the now-defunct Details helped, but Queer Eye helped more. And Kressley, the fashion guru of the show’s “Fab Five,” became the main spokesman. He navigated his way effortlessly from the super-serious fashion shoots of his past to getting sloppy men to laugh at themselves and be open to a cleaner new look. “We’re not here to change you,” he’d assure them. “We’re here to make you better.”
Those five red-hot seasons of doing makeovers on Queer Eye set the stage for his illustrious career. He’s been a judge on eight of the 14 seasons of RuPaul’s Drag Race (and its spin-offs), an Emmy-winning juggernaut that has reached millions of viewers since being picked up by VH1 (it was originally on the Logo channel) in 2017. The reality competition series is currently airing in various versions all over the world.
“It’s a show about sparkles and heels and beauty, but it’s also got a lot of comedy, a lot of heart,” Kressley says. “And you’re rooting for people who have been marginalized, or may have been the underdog. I’ve been so lucky to have worked on two shows that were made by queer people about mostly queer stories. Both really celebrate people in our community and show people out there, especially young people, that there’s a place for you, and you can be successful, loved and celebrated.”
Kressley jets all over the world for his work, knows his way around a red carpet, and lives and breathes the fast-paced and glam lifestyle that comes with 20 years in the TV biz. To keep him grounded, Kressley credits his lifelong love of horses. His grandparents, who lived next door to him growing up, were respected breeders of “all the rage” Shetland ponies, and before he knew it, he was a teenager showing Saddlebreds with his big sister.
“Horses have always been my escape,” Kressley says. “Growing up in the country and being the gay kid and feeling a little bit excluded and different…I never felt that in the horse world. And that’s whether I was showing horses or if I was hanging out at the barn, or just literally, as a 10-year-old, after dinner sitting out there with them munching hay all around you, like 20 or 30 ponies. It sounds like an after-school special and very sad, but it was actually such a wonderful way to grow up. It’s always something that makes me feel at home and at ease. I tell this story that there’s nothing more relaxing than being on top of a horse when you’re trying not to die. You must be in that moment and paying attention to them. You can’t be thinking about your mortgage payment or drama at work or a speeding ticket you just got. You’re only thinking about you and the horse and that partnership. It is a fantastic way to disconnect and have a little mental health break.”
After hosting his inaugural big fashion event in Saratoga, Kressley headed to nearby Pittsfield, MA to meet for the first time his newest horse, Earl, whom he bought via video (on Live with Kelly and Ryan the next day, he joked that he’d been thinking, “What if he’s catfishing me?” after raving about how much fun he’d had at the track in Saratoga). At press time, he was a week out from showing Earl at the World’s Championship in Louisville under his horse’s show name, Flying Private. Kressley’s true love for and comfort around his horses is a sight to see, but he also loves the joy and inclusivity at big events such as horse racing meets, where the affluent horse owners are right there with the grooms, and when the race is on no one cares if you’re there with a day pass or are a trainer at the highest level.
“That’s even more evident in Saratoga, with the picnic areas and the paddock being an area with everyone seated around,” he says. “It’s really one of those places where you can mix and mingle with everybody and just be there for the party. You can just be a fan of it and travel to great places, wear cute outfits, drink mint juleps, and enjoy the camaraderie and community. I don’t think that happens with football.”
After 20 years of mostly makeover work on TV, Kressley is excited about passing the baton to the next generation and branching out in his own career. The super-successful Queer Eye remake is currently streaming six seasons on Netflix, with fashion designer Tan France in the role that Kressley made famous. “They’ve done an extraordinary job,” Kressley says. “Tan is delightful and so lovely. The thing about him is that he’s always finding the best in people, really embracing the person, and is very positive.”
Kressley’s biggest piece of advice for the new Fab Five? “Document everything! Back when we were doing it, we didn’t even have social media to chronicle everything. So I told all those guys to take lots of pictures, keep a journal and enjoy the amazing ride.”
With that behind him, Kressley says he’ll be on Drag Race “for as long as they’ll have me,” and has his eye on landing his own talk show. “I’ve been dabbling with that and doing some guest hosting,” he says. “So hopefully that will be in my future.” Also in his future? “Showing horses, of course. It’s one of the best sports, because you could be 9 or 90 and still do it.”