by Karen Alberg Grossman

To those who maintain it’s impossible to compete in today’s retail world without selling online, check out Mr. Sid! Defying the odds, second-generation Stuart and Barry Segel opened a new menswear store at Boston Seaport last year. It’s doing great, as is their Newton landmark, thanks to the Segels’ heartfelt formula: offer the world’s finest menswear; hire, train and reward the best people; partner with top vendors; invest back in the business; give back to the community; bring in fresh fashion; and keep dreaming up creative ways (wine bar, event space, game room, grooming salon, customer cruises!) to keep clients coming back. Of course, it doesn’t hurt that Stuart and Barry happen to be two of the nicest guys you’ll meet: They’re humble, personable, hard-working, fun-loving and very genuine.

Mr. Sid was founded in 1967 by Bobby Segel; his brother Ira, a successful advertising exec, bought Bobby out a few years later. “It was a contentious situation, and the brothers didn’t speak for some time,” confides Stuart. “Ultimately they reconciled and we learned a lot from the experience. Our dad was a character. He did a lot of great things that set the stage for our culture today: The way he treated customers and vendors, his involvement in the community, his exuberant personality, all created a warmth that still permeates our organization. Ira had tremendous inner strength, was very consistent (perhaps to a fault) and knew how to entertain. (He was serving bagels and hugging customers well before it was in vogue to do so.) But the big change with our generation is the merchandising. While Ira always carried a broad price range that included luxury product, his taste was ultra-conservative. Our mission is to advance our customers from a fashion perspective.”

As is often the case in family businesses, Stuart never intended to join his dad in retailing: He went right from college to law school. “To be honest, our father didn’t really want his sons in the business; he wasn’t all that enamored of men’s clothing himself. And I certainly wasn’t known for my personal style. But when Ira opened a Palm Beach store and needed some help, I took the job and fell in love with it: the constant interaction with different personalities, the creativity, the quality, craftsmanship, and heritage of luxury clothing. I developed a passion, so here I am.”

(Stuart also mentions his passion for golf. “I’m not great—a 16 handicap—and I don’t get to play much these days. But years ago, I was a bartender at a country club so I played all the time. I still maintain that being a bartender is the best foundation for any career, and being a golfer is a great way to reinforce relationships.”)

As for Barry, three and a half years younger, he’d considered joining the family business but wasn’t sure. “Right from college, I went to work for TJX,” he recalls. “It was a great experience but after three years, I realized I’m better at working with people than spending all day in a buying office. So, Stuart forewarned my dad (and took the brunt of his initial anger) but it all worked out. What I really love about retail is that you wear so many hats: I’ve always had a passion for marketing so I was able to pick up where my dad left off.”

Division of labor was never an issue for the brothers: Stuart serves as president, overseeing merchandising but with his hands in just about everything; Barry is VP, heading up marketing, advertising, events and more. “Our dad laid it out that way,” explains Barry. “When we disagree (and we disagree plenty!), Stuart has seniority, and I’m fine with that: He does a great job, and somehow, we manage to respect each other’s opinions.” Adds Stuart, “In a family business like this, you have to set your ego aside, appreciate each other’s talents and recognize that there can only be one president. In truth, our older sister (a lawyer who’s not in the business) is the real boss in the family. I’m grateful we’re all close: We live near each other and spend lots of family time together.”

Apparently, Barry’s easygoing personality helps balance Stuart’s highly competitive nature. In addition to “ultra-competitive,” Stuart describes himself as “intense, loyal and a bit shy. I love to laugh, to have fun, and I go out of my way to ensure that this retail journey we’re on is truly enjoyable to everyone here. Who else would let their employees have a cocktail on the selling floor at 5 p.m.? Maybe that’s crazy but I want our people to love their jobs: Their work satisfaction enhances the shopping experience for our customers. Some of our people have worked here for 40 years, or else they’re 33 years old and have worked here for 10 years. Ira would say don’t get too close to your employees but that’s not me: I want our people to feel part of our family.”

Asked to describe each other, Barry says of Stuart, “He’s a caring person and a terrific manager. Yes, he’s sometimes confrontational because he believes so strongly in what he’s doing, but that’s what makes him a great leader.”

Says Stuart of Barry, “He’s very laid back, which is why we get along so well. Like me, he enjoys the lifestyle we promote: sports, spirits, food, music, travel. But he’s far more charming than I am: I’m convinced that many customers stop by the store just to schmooze with him. He’s caring, sensitive and an incredible father: There’s no finer person than Barry.”

So, will there be a third generation of Segels in the business? Stuart isn’t sure. “Our industry was made up of ‘characters’: It takes a certain personality type to succeed in the clothing business. Of course, it’s different today: It seems even boring people can make a fortune selling clothing online with no inventory but that’s still the exception.” He notes that so far, neither of his kids (18-year-old daughter Rachel, 16-year-old son Matthew) has shown much interest in the business. On the other hand, Barry’s 9-year-old son Jack appears ready to jump on board. “He’s only 9 but he’ d be happy to run the store tomorrow,” quips Barry, adding that “he’d probably turn it into a restaurant.”

On current business, Stuart is cautiously optimistic. “Despite the fast-changing retail scene, our business has been good: double-digit growth for the last four years. Yes, it’s a different market today: We don’t have customers waiting in line for trunk shows or seasonal sales like they did years ago. But considering that in 2008 we lost 40 percent of our business overnight and we managed to build it back up, we’re proud of where we are. Of course, we have the advantage of being virtually the only game in town: There’s no menswear store in the Boston area that does what we do, so we can’t take too much credit. But at this point, we’ve reached a certain pinnacle so we need to figure out what’s next.”

Certainly, building a Seaport store was a bold move. “We’ve always had an eye open for new opportunities,” explains Barry, “and the developer there is a friend and client. The Seaport today is a young, bustling neighborhood with high-end residential and commercial properties going in: start-ups, biotech companies, law firms, financial firms…. Since it’s always been tough to get Boston guys to come out to the suburbs, this seemed the logical move for us.”

“We launched the Seaport store in November 2018,” says Stuart. “The mix is 80 percent the same as Newton, but the 20 percent that’s unique (Faherty, Parajumpers, Patrick Assaraf) is making a huge difference. Granted, the opening has not been without its struggles: A big leak set us back a bit. But in general, we’re really happy with the progress. Our sellers and tailors are terrific, and it’s amazing how many suits are selling—many of them private label.”

Asked about mistakes they’ve made over the years, Stuart singles out their long-ago foray into women’s fashion. “This was back in the ‘70s; we took over the entire lower level, which was probably our first mistake. Mistake #2—we had no solid vendor partnerships in women’s. Mistake #3—we bought too much, too soon. And #4—Poor planning, from sellers to inventories. We stuck with women’s for three years (mistake #5) but learned some good lessons, most notably the importance of being really well prepared.” (So, will they try women’s again? “Never say never,” is Stuart’s response.)

As for today’s biggest challenges, Barry acknowledges the toll taken by casual dress codes. “Most guys don’t have to dress up anymore so our challenge is to inspire them to want to dress up. We find that once they get that first compliment on a modern suit or sportcoat, they want more.” As for the most obvious challenge—the increasing amount of online competition –Stuart still believes luxury customers prefer an in-store experience. (At this point, Mr. Sid has a fabulous website featuring fashion and lifestyle blogs, vendor and event listings, employee profiles and more but they don’t actually sell online.)

“As a smaller retailer, how do we even begin to compete with the big guys, including our key vendors?” asks Stuart. “We’re so much about service, about personal relationships: The only way selling online might make sense for us is if we create exclusive offerings. But with so much product everywhere, we need to be sure that what we offer online is truly special and representative of our direction. For example, it doesn’t pay for us to sell Zegna online; they do a terrific job of that themselves. But when we design our own field coat with Manto or when Andrew designs a demi-boot with Alden—that’s the kind of exclusive niche business we think could work.”

As for the charitable component of their business, (which includes recent collaborations with Heavenly Harvest to donate healthy meals to the hungry and with Fashion Speaks Out to help remove the stigma of mental illness), the Segels show much humility. “When we help our community, we also help our business because our customers value giving back. So, we’re not all that comfortable positioning ourselves as philanthropists. We’d rather just stay behind the scenes, quietly doing what we do.”

I suggest that Ira is likely smiling from heaven. “I hope he is,” says Stuart. “I believe he is.”


  1. Two of the nicest men we will ever have the privilege of knowing.
    Thank you for allowing us to be part in helping your wonderful community!
    The world is better place when you take time to help others.
    We will always be there for the city of Boston and its community.

    1. First, having worked in the ‘90’s as a vendor with Mr. Sid, I am sorry to hear of his passing. He was very much “One of a Kind”, but had an incredible knack for quality and unique design.
      Barry is definitely a chip off the old block, but with a clearer sense of the changing times. Congratulations on the Award!
      Luigi Leonardi
      Former EVP MALO USA

  2. What a great interview! Congrats to both Stuart & Barry!
    Best regards,
    Barbara Roche
    Gravati Shoes

  3. As a former VP at Allen Edmonds they were the place to go to and “Just Look” to see what they were doing and to know what others “should be doing” Although even if you gave others the “playbook” it would not have the sam panache as Mr. Sid. Congratulations

    1. The Segels have always been Good People and talented retailers.
      Congrats on a well-deserved award!

  4. What an inspirational story! Coming from a business around for 37 years like us at The Shirt Box in Michigan, there is so much to learn from each other.
    Wishing you continued success!!!

  5. As someone who knew Ira and Stuart from times being with them at NewYork market time , I read this great article with much admiration for the Stuart family. Being part of a family business all my life and watch my son ( Ken, now fourth generation ) take the business to new heights I have a greater appreciation for what Stuart and Barry have done. I am sure Ira is smiling !!!!

  6. Hello Stuart and Barry,
    Everything that you have shared with us about men’s apparel rings true. Congratulations on your new Seaport Showroom!
    Wishing you continued success with all you do for our business and our community.

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