How Porter Square’s Drinkwater’s built a community, one suit at a time

By Julie Mahdavi

Tuesday, October 7, 2025

Gary Drinkwater in Drinkwater’s, the North Cambridge men’s shop he opened in 2004.

The walk to Drinkwater’s takes me past a mix of casual passersby and storefronts offering the familiar rhythms of everyday retail. At Drinkwater’s, the men’s clothier in North Cambridge, the scene shifts: Two customers in sharp suits step out, pausing to hold the door and greet me with an old-fashioned (I wish I could say current) courtesy that already hints at what’s inside.

Crossing the threshold feels like stepping into another world. I’m reminded of the boutiques of my childhood in Paris, spaces where precision meets elegance, where every detail has its place. Even the merchandise in transition, making way for the new season, blends seamlessly into the shop’s quiet sense of order. The effect is curated and timeless.

At the center of it all stands Gary Drinkwater: dressed impeccably in a tailored suit, pocket square folded just so, embodying the aesthetic his store champions.

He leads me to the third-floor common lounge space, where the bustle of the street below fades. Over the next two hours we talk about everything from his earliest days in retail to the founding of Drinkwater’s in Porter Square in 2004 and the enduring idea of the traditional, timeless Cambridge man who continues to shape his loyal customer base.

The shop sits inside the imposing Henderson Carriage Repository on Massachusetts Avenue, a five-story brick landmark the Henderson brothers rebuilt in 1892 after an earlier structure burned. Built as seasonal storage and showroom for the family’s carriages and sleighs, the building once held as many as 2,000 carriages across its upper floors and stands as one of the finest surviving 19th century industrial buildings in northwest Cambridge. Its “fireproof” mill construction was a pragmatic response to earlier blazes, and today the sturdy brick façade testifies to Porter Square’s industrious past, a fitting, resilient home for a shop that values craft and continuity.

Who is Gary Drinkwater?
Gary is, at his core, a people person. By his own description, he has “the gift of gab” and a love for connecting with others. He started working as soon as he could at 15, ushering at the General Cinemas in the Burlington Mall for a dollar an hour. The perks: free candy, free popcorn and as many movies as he could watch,“the perfect job.” Soon after, he moved into retail proper: first a record shop at 16, then a steady stream of mall jobs where he absorbed lessons about selling, service and customer interaction. His turning point came at Herman’s World of Sporting Goods in the ski department, where he first understood what specialty retail could mean – depth of knowledge, expertise and customer loyalty beyond the transaction.

College in 1971 came after a turbulent decade, and Gary still remembers himself then as a liberal kid with long hair and a hippie sensibility. His patched Lee jeans, which he displays in the shop, have drawn offers of up to $10,000. He refuses to part with them, proof that clothing holds emotional value money can’t measure. 

For Gary, retail is about building bonds with customers, relationships grounded in personality, trust and expertise. “If businesses don’t do this, they won’t survive,” he says. Unlike e-commerce, which strips shopping down to transactions, Gary values the conversations, the experience, the sense of belonging.

The path to menswear
Gary’s career in menswear began in unexpected places. He first worked in visual merchandising, learning how to build a store environment that speaks to customers. As an independent consultant, he helped stores with displays and seasonal trimming. His mother, ever practical, nudged him back toward stability: “You need benefits,” she told him, handing him a Boston Globe clipping for a visual merchandising job at Louis of Boston.

Another candidate landed that role. Louis hired Gary as a seller. “I jumped into luxury goods,” he recalls. He spent 13 years there, absorbing lessons in customer service and the finer points of menswear. It was also where he met Teresa, a sales consultant who would become his wife and business partner.Teresa, who has worked in marketing and PR, helped him prepare for this conversation, Gary says.

From Louis, Gary moved to Cole Haan and then to Stonestreets, a Harvard Square menswear shop. “That was the genesis of my story,” he says. After being laid off from Stonestreets at 50 – the store survived another four years – he faced a crossroads. Having written his first business plan at 25, he had long imagined running his own store, perhaps in Portland, Maine. Instead, with the guidance of the Small Business Association’s Service Corps of Retired Executives program and the mentorship of retail veteran Marty Kress, he developed a plan for Cambridge.

“Marty was surprised I wanted to open a retail store at all, let alone a men’s store,” Gary remembers. “He said, ‘Are you out of your mind?’ This was 2003, when menswear was not doing well and tailoring was doing even worse. But at the end of the talk we shook hands and he said, ’Let’s get to work.’”

By August 2004, after months of planning, Drinkwater’s opened in Porter Square. “One location, that’s all I ever wanted,” Gary says. “Specialty businesses cannot expand. You lose the hands-on, which makes it a specialty store. We’re very happy with one.”

Curating the store
“The store has evolved,” Gary says. “We came through as a moderate-price store with still honest, good-quality goods. The offerings changed as we were able to feel out what the customer wanted. We were constantly listening.”

His own roots in Cambridge helped shape his vision. Growing up in Burlington, he often accompanied his father, who worked in insurance and dressed sharply, into the city. Saturdays in Harvard Square taught him about timeless style and the habits of the Cambridge man. “Cambridge is not fast fashion, not in the least bit,” he says. “We knew we wanted to be an elevated traditional men’s store. We were going to offer value, quality and strong relationships with our customers.” For Gary, that ethos is rooted in the dress codes of the Ivy League in the 1950s and ’60s: fabric-focused, well-tailored, wearable fashion designed to last.

Brands since the beginning
Two brands in particular have been with Drinkwater’s since day one. The first is Engineered Garments, designed by Daiki Suzuki. “Daiki came to Boston in the 1980s to study Americana fashion,” Gary recalls. “On his second day in the city, he went straight to Louis of Boston. I happened to be there, and we struck up a friendship that’s lasted ever since.”

A stack of shirts at Drinkwater’s near Porter Square. The shop has stocked work by New England Shirt from day one.

The second is New England Shirt, whose timeless oxfords Gary discovered through his Louis connections. Another staple has been Paraboot, a traditional French shoemaker. When I mention that my own father bought a pair of Paraboots when Drinkwater’s first opened – and still wears them – Gary remembers him immediately. “Your father is the kindest man and says the most wonderful things,” Gary tells me, an exchange that illustrates why Gary’s customers return year after year. “A lot of people in my life have told me: Pay attention, and it will get you far,” he says.

Do customers know what they want? Do they shop for themselves? Does someone shop for them?
“All of the above,” Gary says. Some customers arrive with a clear idea, others rely on staff expertise. “I don’t blame them, as they simply don’t know what they need. This is where the trust factor comes in. Customers come in, they learn from us, they trust us, and they come back as our items help create a buildable wardrobe.”

The first-ever customer, Theo, still shops at Drinkwater’s. For Gary, that loyalty is proof that expertise and care matter more than any transaction.

Stock and logistics
Much of Gary’s operational knowledge came from his mentor, Kress. “Marty guided me, but I also learned as I went along. He was quite demanding in sharing what really worked and what didn’t.” Shoes, for example, were a point of debate. “I wanted dress shoes in the store, but Marty told me they take up too much real estate. Storing every size in bulky boxes just wasn’t practical for a small shop. So we carry one classic brand instead, Paraboot. It was the right call.”

Any regrets with purchasing inventory?
“Yes,” Gary admits. “I have it right now, and I can’t even give it away.” Around the time of Covid, when athleisure surged, he bought into the “lululemoning” of clothing. “We bought it for a couple of seasons and I should have stopped after the first. Lesson learned.” Still, regrets are rare. “Teresa and I are very intentional in our selections. We do cave in when we’re lovestruck on some items, but we always analyze and focus on our community. They’re the ones who keep us alive.”

The Cambridge man’s aesthetic
“Cambridge men are very frugal,” Gary says. “That doesn’t mean they don’t have money, but they are very conscious of where they spend it.” Surrounded by universities, biotech and tech, Cambridge draws in professionals who value quality and practicality over flash. “We have less of the downtown customers, and more of the conservative dressers. They want classic, timeless clothes.”

Historically, Harvard set the tone. Not that long ago, the university was all-male, and its dress codes, on campus, in clubs, even in leisure, shaped the city’s style. Men gathered in Harvard Square to socialize, smoke cigars and debate; at its peak, the neighborhood boasted more than a dozen men’s clothing stores. Shops such as Keezer’s, which just celebrated 125 years in business (the past seven of them in a space south of Porter Square), are part of that legacy. Drinkwater’s continues it, serving professors, students and professionals with a modern take on traditional style.

How does Drinkwater’s fit into the local economy?
Porter Square wasn’t the trendiest choice for opening the shop, but it had what mattered: accessibility, free parking out back and the opportunity to build a destination. Gary trusted that people would continue to seek him out for the expertise and relationships he had cultivated over the decades, and the shop has drawn customers from surrounding towns. “Yes, we’ve definitely brought more business closer to us,” Gary says. 

From the start, Drinkwater’s new neighbors were curious and excited to see the shop take shape, eager to support something that felt rare and essential: a true specialty store where expertise and care defined the experience. 

Gary Drinkwater’s career in menswear began in visual merchandising, learning how to build a store environment that speaks to customers.

Local support has carried the shop through crises. During the 2008 financial downturn and his Covid closings, customers called not just to shop but to check on Gary and the staff. Some bought $1,000 gift certificates simply to help keep the business afloat. Community, Gary emphasizes, is everything. Even his landlord shops at Drinkwater’s and proved understanding during difficult times. “I like you and I like your store,” the landlord told him. That kind of mutual support, Gary says, is why independent shops such as his remain strong.

The early enthusiasm revealed what many had long suspected: Cambridge needed more independent shops such as this, places that offer not just goods but a sense of belonging. Small businesses such as Drinkwater’s don’t simply add character to the streetscape, but circulate energy and investment, keeping neighborhoods vibrant and resilient. Nearly two decades on, Gary has proven that one well-curated store can do more than sell clothes – it can remind a city of its own traditions while showing how timeless values of quality, trust and connection are always worth investing in.

Drinkwater’s, 2067 Massachusetts Ave., near Porter Square in North Cambridge