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Ron Chereskin is a legendary name in the menswear industry. Starting out in the 70s, he was responsible for transposing his illustrator’s sensibility to the fabrics that were newly available thanks to modern production techniques. His wealth of experience as well as his decades-spanning memory all imbue the collections that he still releases with a sense of historical depth that you might not believe possible in the men’s underwear sector.
“When I started, I was not trained in menswear or fashion. I was a magazine illustrator,” Chereskin told The Underwear Expert in a phone interview. “I was discovered by a shirt and tie manufacturer – they wanted to put illustrations on ties. In the 70s, illustrated shirts were one of the last amazing menswear success stories that ever happened. We did menswear with matching polyester leisure shirts and suits. It was like a uniform.”
“It was explosive!” Chereskin continues. “The biggest moment of menswear there ever was. In an instant, everyone was wearing these polyester leisure suits. It was the first time in many, many years that there was a way for a man to express himself through his clothes. The trend lasted about 10 years.”
His graphic arts training hadn’t prepared him for the speed that the menswear industry moved at, but he liked it: “To me as an artist, I was like ‘wow!’ It was so quick and successful. Before that, I had been doing book jackets and journals and being an illustrator, but this was something else,” he said.
“I loved the energy so much that I went on to discovering sweater machines and got the [Coty and Cutty Sark] awards. Because of my background in art, I used colors never before seen in menswear, like pastels. Back then, men didn’t even wear cotton sweaters, but I started to make them.”
The Coty and Cutty Sark awards were fashion industry awards intended to promote American designers, both of which were
discontinued in the 80s when their sponsors determined that American fashion was already so big that it didn’t need any more promoting. Chereskin took home the Coty Menswear Special award in 1980, and the Cutty Sark award in 1981.
Since then, he licensed his name to a company which used it for a line of basic underwear which in the later 80s competed against Calvin Klein and Tommy Hilfiger, two other Coty and Cutty Sark awardees. “I have great respect for Calvin Klein for bringing [men’s underwear] to the forefront. Now, we have wonderful companies like 2(x)ist and Hugo Boss, but it wasn’t always so dynamic in this sector.”
Chereskin still designs his collections with a commercial illustrators eye towards history. “Each season I do try and think of a theme,” he explains. “You try and look at your history with every collection. I draw from Picasso, Braque, geometric patterns, knits — I’ve done one that’s inspired by the look of the Woody Allen film Midnight in Paris.”
“What I love is to be able to design for men to express themselves. I think underwear has really come a long way in the past few years. Now it’s like a tie — it’s a bit of color and design that you can use to embellish yourself. It’s also very affordable; you can add it to your wardrobe quickly, so it’s a good way for guys to incorporate designer brands into their wardrobe.”
And if this veteran of the modern menswear industry thinks that men’s underwear has come a long way, who are we to disagree?