For Mike Cashen, barbering was never just about hair.
When he opened Pugsley’s Barbershop on Kingston’s Main Street in January 2008, the shop had two chairs, one barber, and a vision rooted in an older idea of what a neighborhood barbershop could be. Nearly two decades later, that vision has grown into two Uptown locations—the original Main Street shop and the nearby Pugsley’s Sideshow on North Front Street—with a team of barbers serving a loyal clientele that has made Pugsley’s Chronogram readers’ number one choice for Barbershop in the 2026 Chronogram Readers’ Choice Awards.
Cashen didn’t open Pugsley’s because market research suggested Kingston needed an old-school barber shop. It was more personal than that.
A self-described “hyper nerd” about the craft, he immersed himself in barbering while earning his license through BOCES, spending countless hours practicing on friends, studying techniques, and obsessing over the traditions of the trade. Barbering, to him, belonged alongside other skilled crafts—tattooing, sign painting, pinstriping—occupations where technique and culture are inseparable. “I was really trying to do it the way I thought was right,” he says, “respectful to the tradition.”
That doesn’t mean treating the shop like a museum piece. Cashen is quick to distinguish between honoring barbering’s past and turning it into a costume party. The classic striped pole, the vintage aesthetic, the straight razors—they’re only surface details. What matters is the role the neighborhood barbershop has historically played as common ground.
One lesson from barber school has stayed with him throughout his career: no religion, no politics. Leave all of that outside. Inside the shop, everyone gets the same chair. “The community can come together and put differences aside,” Cashen says. “Let’s just be in the barbershop.”
That philosophy has proven remarkably durable as Kingston itself has changed.
In 2016, Cashen opened Pugsley’s Sideshow just around the corner from the original shop. Initially conceived as an appointment-only space while the Main Street location continued taking walk-ins, the two shops eventually converged on the same model after the pandemic permanently shifted customer expectations. Today, appointments are booked online at either location, allowing both shops to operate with the same easygoing atmosphere while accommodating modern schedules.
Along the way, Cashen’s reputation has extended well beyond Kingston. For nearly a decade, he’s served as a brand ambassador and educator for the Australian grooming company Uppercut Deluxe, traveling throughout North America and Europe to teach classes, demonstrate techniques, and represent the company at barbering conventions.
Yet for all the travel, Cashen says his favorite part of the job remains the daily conversations that happen in his own chair.
Early in his career, he believed a great haircut was almost entirely about technical perfection. Experience has changed that equation.
Today, he measures a successful visit just as much by the cleanliness of the shop, the friendliness of the staff, and whether clients feel that their 45 minutes truly belong to them. He remembers the stories customers tell him, asks about their families, and picks up conversations months later where they left off. “The longer I’ve been in it,” he says, “the more I’ve been adding to the list of what makes a good service.”
That expanding definition of service may explain why Pugsley’s continues to earn the community’s trust. In an era when so many interactions have been reduced to screens and transactions, Cashen still believes there’s value in simply sitting down, talking with another person, and leaving looking—and perhaps feeling—a little better than when you walked in.
This article appears in July 2026.
