Esquire Barbershop

After Ralph Pressley Sr. died of COVID-19 in July, neighborhood mourners created a memorial for him directly in the spot where he’d cut hair for nearly 60 years (below); Pressley in his clothing store and at work in the barbershop (left).

As one drives down Northwest 54th St. in Liberty City, it’s hard to miss the large white-and-blue building that houses Esquire Barber & Clothing on 14th Avenue. Established in 1961, it’s a local mainstay that remains a sign of Black progress and accomplishment in the city.

The barbershop was the first Black-owned business to open on the street, and it became an emblem for Black folks who were pouring into the neighborhood in droves during the early 1960s after white flight began taking place.

Ralph Pressley Sr., a South Carolina native, moved to Miami in 1958 to look for opportunity. After two years of working and saving money with his wife Geneva Pressley, he opened up Esquire and began working as a barber. Despite the racial tensions that existed (a Ku Klux Klan chapter was operating in the neighborhood when he started), Pressley Sr. got his barbershop up and running. He opened a clothing store specializing in men’s suits and apparel nearly a dozen years later in 1972 at the same location.

Pressley Sr. lost his life to COVID-19 in July, but the legacy he left behind is being upheld through his children, who have kept the community barbershop and clothing store open and running, six decades after it first opened its doors. Ralph Pressley Jr., the eldest son, followed into his father’s footsteps and became a barber at the shop as well. As we sat in the store reminiscing on the life of his father, I could tell that Esquire is a place of joy and camaraderie among the denizens in Liberty City.

“He always wanted to help and give to people,” said Pressley Jr. “He gave a lot of jobs to people in our community. He dealt with a lot of politicians, churches, kids and community groups. For the community, he represented the truth.”

The love Pressley Sr. had for this enclave emanates from the store’s interior. Frayed postings with newspaper clippings on the accomplishments of Liberty City are displayed throughout, and I noticed an interesting Barbers for Obama poster proudly tacked onto one of Esquire’s orange walls. His son shared that customers of the shop were always impressed with his father’s stellar service, consistent business opening hours, and positive attitude among folks young and old.

Pressley Sr. often told his sons that he wanted the shop to be generational and remain a part of the family legacy. He often spoke of his early life in South Carolina, where his only opportunities were to work on a farm or become a carpenter. He learned the barber trade on the weekends after spending the week working on his father’s farm. Thus, the store was an extension of Pressley Sr.’s passion. His proudest accomplishment was remaining in business for so many years, which took dedication, patience and love.

Ralph Pressley Sr., the late founder and owner of Liberty City’s Esquire Barber & Clothing, would often host checkers competitions in the …

The shop’s longevity has made it a comforting staple for people in the community. In a corner of the store, there is a checkers table set up where folks can come in and play games. Indeed, hosting checkers competitions in the store was a normality for Pressley Sr., as were regular discussions on current events among those who frequented it. Customers would affectionately call him “Dad” and he would make sure to always model good behavior before them.

Esquire Barber & Clothing continues to serve Liberty City, selling men’s apparel, offering socially distanced barber services and providing a familiar hub to which community members can gravitate during a time of uncertainty and unrest, even after the death of its founder – exactly as he would have wanted.

“My fondest memory of my father,” said Pressley Jr., “was watching him walk into the shop every day.”

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