I’ve been in the retail world my entire adult life. After art school, I traded in my paint brushes for a merchandising manager role at a sporting goods store, moonlighting as a window dresser. Then, fate stepped in. My mom tipped me off about a window dresser position at Louis Boston, the renowned high-fashion menswear store. Although that job was filled, my sales background landed me on the selling floor. Louis Boston was an internationally known high-fashion menswear store and one of the first retailers in the United States to carry clothing by Ermenegildo Zegna, Gianni Versace, Giorgio Armani, Paul Smith, Gianfranco Ferre, and Dries van Noten, along with the Kiton and Brioni lines.

My time at Louis was deeply influential, it was at Louis Boston that I met my wife, Teresa. It is where our shared passion for style and quality brought us together, and unbeknownst to us, created the foundation that would later bring our dream of creating something unique to life. Under the owner’s mentorship—the incredible Murray Pearlstein—I soaked up everything about the industry while accompanying him on buying trips. He was my greatest mentor and his guidance was invaluable, shaping my understanding of the business.

After leaving Louis and helping other stores find their footing, it was time to strike out on my own. In 2004, with the support of family and friends, Drinkwater’s was born when Teresa and I opened the doors to our store in a space within a historic 19th-century carriage factory building. With antique French furniture and a meticulously curated selection, we aimed to redefine menswear in our own vision. But none of this would have been possible without the support of our community—from close friends who believed in our dream to family who pitched in with everything from capital to hands-on craftsmanship during the build-out.

Since it’s a small space, we made sure it was extremely well edited, our product is reflective of not only who our customer is but of our vision of what style is and should be.

Our journey has been shaped by dedicated employees who started as novices and grew into seasoned style consultants. They are the heart of Drinkwater's, embodying our ethos of impeccable service matched only by the quality of our products. Whether outfitting a groom for his wedding or helping a graduate find his first suit, these moments of connection with our customers have defined our purpose.

In an era dominated by e-commerce, we've stood firm with a blend of exceptional service and superior products. Our commitment to timeless elegance, coupled with a keen eye on durability and comfort, has allowed us to thrive amidst changing trends. We've embraced agility, constantly updating our offerings while staying true to our vision of enduring style over fleeting fashion.

The past two decades have been a whirlwind of milestones, from building relationships with our community to weathering challenges like the pandemic. The outpouring of support during those tough times was truly humbling. It's been a privilege to be part of our customers' lives.

Looking ahead, as we celebrate this milestone and embark on the next 20 years, our commitment to quality and style remains unwavering. We extend heartfelt gratitude to our loyal customers, dedicated staff, and invaluable partners who have been integral to our success.

We can't wait to see what the future holds as we continue this adventure together, always striving for the perfect blend of style and substance in menswear.

Cheers to 20 years of style, and an amazing journey!

Warm regards,

Gary & Teresa Co-Founders & Owners, Drinkwater's Cambridge