With warm lather, straight razors, 1920s-era Koken barber chairs and a seasoned group of barbers, Phil’s Hairstyles on Wall Street has been keeping Yalies and locals looking sharp since 1924.

91 years next to Yale has left more than a few souvenirs at the shop. A picture of the 1934 school hockey squad hangs on the wall, among several other sepia teams. Another image shows former Yale president Rick Levin and current president Peter Salovey at a Halloween party. A signed photo of a different kind of president, George H. W. Bush, hangs above the counter. He got his hair trimmed at Phil’s while studying at Yale, later returning for a cut during one of his presidential runs.

Like the highest office in the land, Phil’s has traded hands over the years. Longtime Phil’s barber Carl McManus, in a 2012 interview with the Yale Herald, recalled a time not long after the business—by then a three-shop local chain—had left original owner Phil Catania’s hands for those of two of his trusted cutters, Joseph LoPresti and Rocco “Rocky” D’Eugenio. “When I started , they had ROTC here, and we were always busy. They were on the floor, the students, because the waiting chairs had filled up. And then the late ’60s, with the long-haired hippies, hurt a lot of businesses. … The students didn’t get haircuts.” Speaking about the flagship Wall Street location, where he and D’Eugenio worked together, McManus said, “So it went from five barbers down to two—just the boss Rocky and I. It was really tough.” According to a 1988 article in the New Haven Register, the lengthening of Yale’s locks also trimmed Phil’s from three locations to two. As of this past winter, only the flagship Wall Street location remained.

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Today, Phil’s has about a dozen barbers, both full- and part-time, and, since April, a second location at 55 Whitney Avenue to spread them across. Current owner Pasquale DeSisto, who took over in 1996 from D’Eugenio and LoPresti’s wife Lillian—who in turn had taken over her husband’s share following his death in 1993—opened the Whitney shop with his younger brother, Silvio DeSisto, rekindling a partnership that started, then stopped, decades ago.

The brothers, born eight years apart, began learning the barber’s trade in Alife, Italy, at the tender ages of 12 and 7, respectively. Instead of scissors and straight razors, they first paid their dues with brooms, dustpans, wash cloths. “Our boss worked us so hard, we barely ever sat down,” Silvio says. Staying on your feet, he remembers being told, is the only way you learn.

After four years on his feet, Pasquale had learned enough to open his own barbershop. A couple years later, he put Silvio, then 13, in charge of a second shop. Teenagers with razor blades—what could go wrong? “I didn’t kill nobody,” Silvio says, laughing, although once, while training another boy in his shop, Silvio bumped a misplaced blade, giving the man in the barber chair a big cut across the forearm. “It was alright,” Silvio says. “Back then, people didn’t sue much.”

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By the time they left for America in 1963, the brothers were running three Italian barbershops. Selling them to help finance their journey, the brothers intended to join forces once again in America, but opportunity parted them.

Pasquale and Silvio began working at two different barbershops where, eventually, each took over. For 43 years, they operated separately. Then, in 2007, Silvio was given an offer to sell his West Haven shop, which he’d renamed Silvio’s, for a sum he “couldn’t refuse.” But instead of retiring, he went to work for his brother again, just like old times.

Well, almost. Silvio recalls working for his brother as a kid: “He was a pain in the ass back then.” “Now he’s a pain in the ass,” Pasquale retorts. But despite occasional jabs, they don’t seem to harbor any real grudges. What they do have between them is over 120 years of barbershop experience.

At the Whitney location, I decided to see what $19 and nearly 60 years of standing behind the chair could do for me. After a spritz, a combing and an assessment of my curls, Silvio said, “You’ve got difficult hair,” to which I said, “I know.” Juggling scissors, comb and conversation, he lathered the back of my neck with warm foam and scraped it with a cool, straight razor. He cleaned the blade and then ran it through my hair. “Makes it easier to comb,” he said. When the barber’s bib came off, the mirror showed a new man who liked the way he looked. And for a good price, too. (Becoming a new woman at Phil’s takes a bit more—$35 for a cut.)

Why is a good haircut so satisfying? Maybe it’s in part because, as Silvio suggests, good haircutters are hard to come by. “They don’t make them,” he says, “like they used to.”

Phil’s Hairstyles
82 Wall St, New Haven (map)
Mon-Tues 8am-5:30pm, Wed 8am-5pm, Thurs-Fri 8am-5:30pm, Sat 8am-4pm, Sun 10am-3pm
(203) 865-9187
55 Whitney Ave, New Haven (map)
Mon-Fri 8am-7pm, Sat 8am-5:30pm, Sun 10am-3pm
(203) 495-8666

Written and photographed by Daniel Shkolnik.

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