It’s fitting that the winner of East Hampton’s first Holiday Spirit storefront-décorating contest should be a business known for having fascinating windows: The Monogram Shop on Newtown Lane has made national headlines not for its holiday décor but for the tally of political plastic cup sales that, in election cycles past, has been a notoriously accurate predictor of presidential outcomes. The window cup count was wrong in November, but the window display in December is, according to a panel of judges, oh so right.
“Vanity Fair, The New York Times, The Post, Wall Street Journal — they all covered the cups,” said Sophie Menges. She runs the shop alongside her grandmother, Valerie Smith of East Hampton Village, who founded it with her own mother in 1997. The dishwasher-safe Trump drinking cups, with an orange-haired president-elect in profile, undersold the Harris-Walz cups by a significant margin, marking only the second time the Monograph Shop bellwether has been incorrect, Ms. Menges added.
The winning windows this winter season feature gingerbread-house models of the Mulford Farm farmhouse and East Hampton’s Long Island Rail Road station baked by Molly Mamay, and a Hook Windmill made of Hershey’s Kisses. Plaid Christmas stockings are strung above with care, and there is a red truck bearing gifts, bright boughs of red berries, and one of the big, plush teddy bears that has become another Monogram Shop signature. The bears, which come with a small cotton roll-neck sweater personalized with a child’s name, are a perennially best-selling baby gift: The baby wears the sweater until he or she outgrows it, at which point it is worn by the bear.
The Monogram Shop isn’t so much a mom-and-pop shop as a mom-and-grandmother shop. Like much of the wares, the bears and the stockings are linked to family tradition. When the store first opened in the 1990s, Ms. Smith’s mother, Constance Hoagland, created the handmade needlepoint Christmas stockings sold there, as well as hand-hooked rugs. Mrs. Hoagland, who died at 98 in 2022, was a familiar presence in cardigans and pearls at the front counter where her great-granddaughter now greets customers.
Ms. Menges said she had returned to the family house on Buell Lane from New York City to keep the family business going for another generation: “It’s important!” she said on Saturday, as customers perused cocktail napkins with humorous slogans (“Forced Family Fun” and “Stop Talking”) or came in carrying pillows to be personalized by an embroidery expert seated at the monogram station at the back. An aunt, Hadley Cooper, runs the business’s website from home in Washington, D.C., and Ms. Menges’s mother used to run a Monogram outpost in Locust Valley.
The Holiday Spirit contest was a collaboration between The Star, the Anchor Society, and the Greater East Hampton Chamber of Commerce, with judging on Nov. 30. The judges were Barbara Layton for the Chamber; Tom Osborne representing the Anchor Society; this reporter on behalf of The Star, and Lisa Frohlich of James Lane Post. A second round of voting became necessary after the first round of judging turned up a three-way tie among the Monogram Shop, Kumiso restaurant (which donned a bright pink garland to match its logo), and Eastman Way, the recently rejuvenated alleyway beside Starbucks and shops facing Park Place that has become a twinkling winter wonderland.
Honorable mention went to London Jewelers, a garland-decked landmark at the heart of the shopping district; Obligato, with a Pop Art hot-pink tree; and Dayton Ritz Osborne insurance agency, with a classic Father Christmas and icicles. Bonpoint, Diptyque, White’s Apothecary, and Brunello Cucinelli also drew appreciative nods. The judges were impressed that even a few real estate offices, not known for bedazzling their windows in years past, got into the festive spirit: Brown Harris Stevens tied gigantic gift-wrap bows on its doors, and Corcoran has white and red candy-striped columns.
The three Ralph Lauren boutiques on Main Street were universally acknowledged by the judges to be the standout stars of holiday-window dressing, on another level altogether. But this truth sparked a bit of mild controversy on the panel; in the end, it was decided that the rules will be further refined next year to define what to do about professionally outfitted versus amateur efforts. The Ralph Lauren company, meanwhile, was the sponsor of a second window-décorating contest, hosted by the East Hampton Village Foundation during Saturday’s Santafest, with cash prizes awarded to the charity of the winners’ choice.
Born out of a letter to the editor and subsequent editorial in The Star last winter, the Holiday Spirit competition aimed to encourage warmth and cheer in the central business district, where — as residents and tourists alike have complained for at least two decades — too many shopfronts are bare-windowed and barren between Columbus Day and late spring. While only perhaps half the businesses in the core shopping district have décorated their exteriors this holiday season, still, there has been an unmistakable uptick in evergreens, wreaths, red ribbons, baubles, and bows. Coupled with the Santafest market and parade and the greenery-wrapped lampposts, the village was a veritable elf-a-palooza by Saturday.
The Monogram Shop, whose operators were also applauded by the judges for remaining open for business around the calendar year, rather than locking the door and hanging up a “See You in Spring” sign, won two prizes: this newspaper feature and a huge basket of cheer. The gift basket held South Fork wine, prosecco, and spiked eggnog donated by the Anchor Society, and swag from The East Hampton Star and several Chamber of Commerce members, including Carissa’s the Bakery, the Hamptons International Film Festival, the Y.M.C.A. East Hampton RECenter, the Roundtree of Amagansett, Claire V., Align Yoga Hamptons, Il Buco Vita Café, and Alimentari.
“We loved the gift basket,” Ms. Menges said. “All four of us who work in the shop split it. It was thoughtful and sweet.”