For luxury men’s retailer Mr. Sid, the Seaport feels like a tailor-made fit. Stuart and Barry Segel, brothers and co-owners of the Newton-based family venture, are opening a second menswear shop in One Seaport Square by early next month, right on the heels of the institution’s 50th anniversary. “We’re very proud that we’ve sustained a three-generation family business for 50 years,” Stuart says. Though the pieces they sell—crisp shirts by favorite designers, bespoke suits, heirloom-worthy leather shoes—are an undeniable draw, the brothers credit their success to their ties to the community. “It comes down to relationships with your clients and friends,” Barry says. “Ultimately, they become part of the fabric of your business.”

The duo was drawn to the energy of the Seaport and neighboring Fort Point, and the 2,200-square-foot spot is a reflection of both the surrounding modern glass and chrome structures and historic brick wharf buildings, blending handsome woodwork with modern, clean lines. The layout is a kind of optical illusion, with a series of wood-framed doorways leading to room vignettes, including a bar in the back where shoppers can grab a bourbon before they browse. Boasting the same offerings as the Newton flagship, the store includes a tailor shop, made-to-measure services and a trove of swatches for shirts, suits and sportswear. With Seaport Barbers adjoining the space, it’s easy to imagine a scruffy, style-challenged customer stumbling in, and then hitting the sidewalk with his new Italian leather shoes and fresh fade.

Even with five decades on the books, there’s the new thrill of discovering who the Seaport customer is. “You have the millennials here, but you also have the guys who work at places like Vertex and are more established, who might live in the suburbs,” Barry says. The key is to offer items that resonate more with the city guy, along with timeless mainstays. But Stuart has spotted a shift in menswear during the past six or seven years: “You see that a lot of the more traditional businesses like banking and private equity have gone to business casual.” Which is not to say that customers are getting lazy in their threads, but that they’re on the lookout for quality—like custom-made options cut from luxe fabrics—when it’s time to suit up.

Photo Credit: Heather Prohaska

How to wear a classic navy suit

Both Stuart and Barry Segel agree that a classic navy suit is a piece that every guy needs in his closet. Here are their tips on how to wear and style this staple.


“A navy suit is very versatile. It can be worn with black or brown shoes and can be dressed up or down,” Stuart says. Barry adds a tip for the frequent traveler: “If you don’t have a lot of room to pack, you can bring a solid navy suit with you and wear the jacket as a blazer with a pair of jeans.”


“You want the back of your jacket to just cover your rear end,” Barry advises. “Today, sleeves are running narrower and with a softer shoulder. We recommend showing a bit of cuff.”


Have a little fun with your look by skipping the standard white shirt. “You can wear checked shirts or even a beautiful knit underneath,” Barry says. The daring can finish off the suit with one of Barry’s favorites—a pair of colorful suede shoes.

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