Windsor of Old Town—39 Years of Elegance in Old Town

When Donna Windsor opened her shop on Valentine’s Day in 1981, she couldn’t have known that by the time 2020 rolled around she’d be celebrating 39 years open!

The Gentlemen’s Quarters set a new trend in salon care for men. (Photo: Stephen Windsor)

Alexandria, VA – When Donna Windsor opened her shop on Valentine’s Day in 1981, she couldn’t have known that by the time 2020 rolled around she’d be celebrating 39 years operating Windsor of Old Town, outlasting scores of nearby businesses that opened and closed in the process.

Windsor had been running a salon for five years in Rosecroft, Maryland, when friends urged her to move her business to Old Town. After visiting the area for a day of shopping, Windsor moved in and set up shop at 107 South Union, with a lovely view of the Potomac River. Her building probably dates to the 18th century and contains the first spiral staircase built in the United States. “Moving here was such a gift, a blessing,” Windsor says. “I’m eternally grateful to my friends for encouraging me to come here. I can’t believe it’s been 39 years. The time has just flown.”

Windsor of Old Town’s original logo by acclaimed local artist Todd Healy.

Having that kind of longevity in Old Town is impressive. Windsor, who owns the salon and adjacent Gentlemen’s Quarters with her son, Stephen, cites a few reasons for their success. “You must be present, on site, every day,” she explained. Not only for the customers but also, and perhaps more important, for the staff. Windsor stays in close touch with her staff, interacting daily to keep the lines of communication open and flowing. Weekly meetings offer the chance to brainstorm new ideas and solve any lingering issues.

Windsor listed additional, essential lessons she’s learned: Be progressive: stay current with education, industry techniques, and style trends. Be diligent: keep all business accounting and records in house. Be innovative: embrace social media and all channels of communication. Be independent: stay involved and effective, trust yourself, and follow your instincts.

Donna’s son Stephen joined the company in 1995, which inspired her to try an idea she got after seeing an ad for a man’s haircut. No salons nearby were catering to men at the time, so they repurposed part of their space and opened the Gentlemen’s Quarters.

Stephen and Donna Windsor. (Photo: Susan Fleischman)

It was a visionary move, way ahead of its time, and one of their most successful endeavors. According to an article in GQ magazine, men-focused salons accounted for 29 percent of the market in 2005. By 2017, that share had jumped to 49 percent, and continues to grow, thanks in no small part to the exposure and explosion of social media.

“Of course men care about their looks; why wouldn’t they?” Windsor says. “They enjoy the extra services we offer, such as manicures and pedicures, and they appreciate the privacy of our Gentlemen’s Quarters.” She credits the expansion as instrumental in helping the business survive the ebbs and flows of client turnover, generational shifts, and operational challenges.

The Gentlemen’s Quarters is at your service. (Photo: Susan Fleischman)

Many clients, some quite well known, have been loyal for years. Windsor of Old Town is a convenient step away from the bustle of D.C. for politicians and pundits, as well as Washington Nationals and Capitals coaches and players. Goalie Braden Holtby, “sincerely the sweetest guy, so friendly and unpretentious,” is a client. Windsor had a commemorative drawing of Holtby’s famous stretched-out save from the Caps’ 2018 Stanley Cup win, and she asked Holtby to sign it so she could give it back to the artist. A second copy of the drawing hangs in the salon as well, next to a photo of Holtby holding the signed print.

Windsor has thought about her business’s 40th anniversary looming in the distance, but has not finalized plans yet. “Certainly, there will be a party,” she says, “although what do you do for something like that? Besides give thanks for our work and our success, which we really do every day.”

Words to live by at the entrance to Windsor of Old Town and the Gentlemen’s Quarters. (Photo: Susan Fleischman)

Windsor of Old Town and the Gentlemen’s Quarters are located at 107 South Union Street in Old Town Alexandria, (703) 836-7330.

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