Next time you find yourself in Copley Square, look up at the names etched in marble just beneath the cornice of the Boston Public Library. Tucked between Byron, Milton, and Shakespeare, you’ll spot Motley—my surname. My great-great-grandfather was a writer from Boston. A fine scholar, to be sure, but I suspect he bribed someone to land his name beside the Bard.
As my Ukrainian girlfriend says, I’m like British snow on a paper plate slathered with mayonnaise. And if we Boston Brahmins know anything besides croquet stratagems and trust fund litigation, it’s preppy clothes. Hell, I probably came out of the womb in a pink bow tie and boat shoes.
I shed my preppy plumage in college—it was cooler to be a hippie—but I re-embraced it when I moved to New York City as a thirty-something bachelor. Sporting seersucker, needlepoint belts, and Nantucket red shorts, I’m something of an exotic creature in Brooklyn.
Time-honored preppy labels are the antithesis of fast fashion. They make clothes that are timeless in style and so well made they’ll last for generations. And if something does rip or break, the L.L. Beans and Vineyard Vines of the world will often replace it, no questions asked—how’s that for gentlemanly manners?
Photo via Vineyard Vines
Vineyard Vines
Shep and Ian Murray left the wilds of high finance in New York City to chase the good life on Martha’s Vineyard. In the early days of Vineyard Vines, they sold hand-stitched neckwear—pastel-colored, silken sartorial confections—straight from their boat in Edgartown Harbor.
Since then, the brand has expanded to include everything from sport jackets and denim to oxford shirts and cufflinks. You can bet that any garment bearing that little pink whale is comfortable, dapper, and meticulously crafted.
The writer's go-to Randolph P3s
Photo via Randolp
Randolph
Moving inland from Martha’s Vineyard to the Boston suburbs, Randolph Engineering is the best-kept secret in luxury eyewear. Aviators are Randolph’s signature frames, and they have been a contractor for the U.S. Department of Defense since 1980. Randolph crafts its eyewear from jewelry-grade metals, and with gleaming satin-gold rims, they look luxurious even from a distance. Aviators don’t fit my face well, but the P3’s, delicate circle frames in iridescent hues, are my staple shades to wear with casual attire.
Photo via B. Draddy
B. Draddy
A lacuna in my preppy credentials is that I never picked up golf. (I was too busy competing in real sports like wrestling.) But I do admire the game—the historical connection to Scotland, communion with nature, and, of course, the handsome attire of high-end golf brands.
B. Draddy blends vintage country club charm with masterful tailoring. If you’re in the market for a cashmere sweater that won’t break the bank, you can’t do better than B. Draddy. Their polos, chinos, and pullovers are designed for the links, but they’re equally suitable for lounging in an adirondack chair on the clubhouse veranda with a bourbon in hand.
Photo via Kiel James Patrick
Kiel James Patrick
Preppy mainstays like Brooks Brothers and Ralph Lauren politely nod to New England’s maritime heritage. Kiel James Patrick embraces it with the enthusiasm of a Newport divorcée who’s just drained her fifth Chardonnay and spotted the shirtless pool boy.
Founded on the craggy shores of Rhode Island, KJP specializes in jewelry, watches, and apparel adorned with playful nautical motifs like anchors, signal flags, and sailors’ knots. Golden retrievers, lobsters, and other New Englandy emblems add a touch of swagger to their cable-knit sweaters and needlepoint belts. KJP also makes handsome and affordable men’s watches. For my money, The Adventurer is one of the prettiest timepieces under $500 on the market.
Photo via Southern Scholar
Southern Scholar
Hailing from Texas, Southern Scholar makes dress socks so comely they could make a buttoned-up New Englander holler yeehaw. The patterns lean classic—chocolate and chestnut tones dressed up with herringbone, stripes, and tattersall. Best of all, they stay put—no slipping, sagging, or bunching around the ankle like lesser hosiery.
Pair them with Southern flair—like a seersucker suit or a waxed hunting jacket—and, hoss, you’ll be the most dapper gentleman from Charleston to Chattanooga. My only suggestion is that they name the next release after William Faulkner or Hunter S. Thompson—Southern scholars of the highest order.
Photo via Robert Talbott
Robert Talbott
I think of Robert Talbott as the West Coast cousin of Brooks Brothers—preppy and luxurious, with a kiss of California sunshine and laid-back charm. It’s the sartorial equivalent of a Californian in the Ivy League who’s never stressed, always tan, and inexplicably lands a hedge fund gig after graduation.
Founded in beautiful Carmel, California, Talbott crafts oxford shirts, neckties, and sport coats that epitomize West Coast luxury. The best pair of summer chinos in my wardrobe are from Talbott—they fit like a dream and are light enough to keep cool when the mercury climbs in New York City.
Photo via Rose & Born
Rose & Born
Scandinavian fashion isn’t traditionally preppy, but the two sartorial genres share common hallmarks: elevated craftsmanship, clean lines, and understated luxury. Based in Stockholm, Rose & Born is like an Ivy Leaguer who studied art history in Europe on a Fulbright—preppy with a touch of Continental polish. Their made-to-measure sport jackets, tailored from Italian fabrics, are elegant without being ostentatious—garments fit for a Swedish business mogul with a connoisseur’s palate for Champagne. Rose & Born’s sunglasses and footwear likewise embody Scandi-chic.
