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Like many kids his age, Pierson Senior Sam Guest is finishing school and applying to colleges, but the 17-year-old’s unique creativity and entrepreneurial spirit has driven him to accomplish things most teenagers only dream about.
After years of hard work and false starts, Sam has established his own brand of artistic T-shirts, and he’s selling them at a cutting edge boutique in Sag Harbor.
“I started it when I was in sixth grade,” Sam said, recalling when he designed his very first shirts. At the time, he and a classmate, Joe Nascali, envisioned creating a skateboard company, which they called, “Tribute.” Six years later, Sam has kept the name, but he’s sticking to T-shirts, not skate boards, and he’s doing things on his own.
The first shirts were simple, with designs made using only a Sharpie permanent marker and sometimes spray paint, Sam said, explaining that he and Joe made them for friends and family. “They all loved them,” he said, noting that despite the reaction, he’d never thought to sell the shirts until a couple of years later.
The young designer credits his mother Deirdre Guest as his biggest fan and supporter, and he said it was only with her encouragement that he began to elevate his business to the next level. In eighth grade, when he was just 13, Sam produced a line of two shirts and sold them at Island Surf in Sag Harbor, where he worked. It was a huge accomplishment for such a young man, but he said the experience did not go as planned.
Sam said the shirts were not printed the way he’d designed them and he was disappointed in his graphics. He’d drawn an Aztec motif for one shirt and an Indian in a headdress for the other, but the images looked “hand drawn,” and left Sam frustrated. “That really discouraged me from doing it at all,” Sam said, noting that he perceived his shirts as somewhat of a failure and that, combined with the emergence of two other local T-shirt designers, Lola and Edgewood Goodies, whose shirts are also sold at LABL, almost caused him to give up.
Sam created the three designs he now sells at hip street wear boutique LABL in Sag Harbor less than a year ago, when his mother, a veteran of the fashion industry in New York, prodded him to try the T-shirt business again. He got back to creating shirts in March and by the end of last summer, Sam had 300 printed and ready for distribution.
“I got these three designs and really learned to Photoshop them,” Sam said, explaining how he was finally able to make the quality images he’d always wanted through a computer program that had been previously unavailable. Instead of the hand drawn look he reviled, the new designs had thicker, more graphic lines.
With the help of Ms. Guest, Sam was also able to find a printer who screened each shirt by hand, which assured that the images would be placed exactly where he intended.
“I’m really, really specific,” Sam said, remarking on the importance of placement. “When you look at my T-shirts, every one is different,” he said, noting that the hand placement made each shirt slightly unique, imperfect and more customized. All of them have slight variations, including stray drips of screening inks and minor shifts in placement, though they are all within the area he intended.
One of Sam’s designs, sold for $48 at LABL, is based on his earlier work, with various images, including a boom box, lightning bolt, giraffes, anchor, lettering, clock and smiling mouth, among many others. The layered pictures are massed together along one side of the white shirts and appear as though drawn with a marker. His company name, Tribute, is also on the shirt in block letters, nicely juxtaposed against the messier doodles.
Sam’s second design is available on both purple and white shirts and features the image of a woman’s face in heavy black lines distorted by comic book-like Benday dots, much in the spirit of Roy Lichtenstein, though clearly not a direct translation. The designer said he created the image using a simple Macintosh program then imported it into Photoshop for more advanced manipulation.
The simplest design is also Sam’s most popular. He said his gray or white shirts featuring only text that reads “The Finer Things” in gold and white or gold and black lettering have been the bulk of the dozen or so shirts he’s sold through LABL up to this point.
Sam intends to go to art school and study photography, but he said that doesn’t mean his T-shirt company is dead. “I’d love to establish Tribute too,” he said, noting that the fledgling company remains a big part of his life. Sam’s portfolio was accepted at the Art Institute of Chicago and he’s applied to the Museum School in Boston.

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