Planning

A Very Gatsby Christmas: Inside Over The Moon’s Great Holiday Gift Guide at Old Westbury Gardens

Cathleen Freedman

October 28, 2026

Step inside the storied Gold Coast estate that inspired our 2026 Holiday Gift Guide, where the silver is polished, the presents are piled high, and Christmas morning is an occasion worthy of Daisy Buchanan herself.

*Luciana Emilia dresses and Sanoë blazers on the lawn of Old Westbury Gardens.*

The Great Holiday Gift Guide has arrived, and this year, you’re invited to spend the holidays in East Egg.

Picture a Christmas morning filled with gleaming crystal, sparkling silver, Ginori 1735 china at every place setting, a towering tree dressed in its holiday finest, and a mountain of ribbon-tied presents waiting to be unwrapped. Outside, the lawns stretch toward the horizon, and somewhere in the distance, a green light glows across the bay.

When dreaming up this year’s Holiday Gift Guide, the Over The Moon team had a very particular kind of Christmas in mind—one with all the glamour of the Gilded Age, a healthy dose of nostalgia, and enough holiday magic to make even Jay Gatsby believe in happy endings.

Naturally, there was only one place to bring the fantasy to life: Old Westbury Gardens, the magnificent Long Island estate whose grandeur helped inspire Baz Luhrmann’s 2013 adaptation of The Great Gatsby.

And so, with clothing racks filled with Emilia Wickstead and Sanoë, a Christmas tree ready for trimming, and more beautifully wrapped presents than we could count, we decamped to Long Island’s storied Gold Coast to create our most festive Holiday Gift Guide yet.

*A proper holiday wardrobe includes dresses from Delphine and Simkhai that can be worn around the home or on the town.*

A House With a History

As it turns out, Old Westbury Gardens has a love story of its own. And fittingly, it begins with a gift.

In 1903, businessman John Shaffer Phipps promised his fiancée, Margarita Grace, that he would build her a home reminiscent of her family’s English estate at Battle Abbey. Four years later, the couple moved into Westbury House with their young children, beginning a new chapter in a home that would become one of Long Island’s most celebrated estates.

Today, the property encompasses more than 200 acres of formal gardens, sweeping lawns, tranquil ponds, and tree-lined allées. Inside, frescoed ceilings, grand rooms, and a light-filled solarium offer a glimpse into a bygone era when entertaining was practically an art form.

The estate’s history is every bit as glamorous as its architecture. The Phipps family commissioned a portrait from John Singer Sargent, and over the decades, the house and gardens have played host to countless celebrations, cinematic moments, and, more recently, some truly spectacular weddings.

The 2026 Holiday Gift Guide has something for everyone: La Coqueta for the littles, Bauble Stockings for the mantel, and treasures aplenty, all adorned in Inner Child wrapping paper.

A Star in Its Own Right

If Old Westbury Gardens looks familiar, there’s a good reason. The estate has enjoyed a rather illustrious career on the silver screen, appearing in films including North by Northwest, Love Story, The Age of Innocence, Cruel Intentions, and American Gangster. Eagle-eyed viewers may even recognize it from Gossip Girl.

In the name of research, OTM Founder Alexandra Macon rewatched Cruel Intentions the night before the campaign shoot. One of her main takeaways? She still can’t believe her parents let her watch it when it first came out.

Of course, Old Westbury Gardens has also had its fair share of romantic leading roles. Most recently, it served as the setting for Paige Lorenze and Tommy Paul’s spectacular summer wedding, a celebration planned by OTM Directory member Easton Events that made the most of the estate’s extraordinary beauty.

“The moment we visited Old Westbury Gardens, I knew I didn’t want to compete with its beauty,” Paige told Over The Moon. “I wanted every detail to feel like it belonged there.”

It’s a sentiment we took to heart when dreaming up our own holiday celebration.

*Paige and Tommy Paul’s wedding at Old Westbury Gardens. Photo: Kayleigh Taylor*

Christmas Comes to East Egg

For our 2026 Holiday Gift Guide, we imagined what Christmas might look like if the Buchanans had spent December 25th at Old Westbury Gardens. The answer? Beautifully set tables, presents stacked beneath the tree, festive fashions for every occasion, and more than a little holiday extravagance.

Bringing it all to life was no small feat, but with the help of OTM Directory Planner In Any Event, Old Westbury Gardens’ exclusive planning team, and Noble Diaz Events, who worked their magic on the florals and décor, the historic estate was transformed into our very own Christmas wonderland. From the festive finishing touches to the beautifully considered details throughout, both teams went above and beyond to make the holiday fantasy a reality.

There were ornaments to treasure for years to come, gifts for the consummate hostess, little luxuries for the people who have everything, and thoughtful finds for everyone else on your list. In other words, all the makings of a very merry Christmas.

But beyond the silver and sparkle, we wanted to capture something that feels particularly special about this time of year: the rituals we return to, the people we gather around the table, and the joy of finding a gift that feels as though it could only have been chosen for one person.

After all, the best presents have a way of becoming part of the story. An ornament unwrapped each December. A set of china that makes its appearance every Christmas Eve. A beautifully embroidered stocking that follows a child from one home to the next.

That’s the spirit behind The Great Holiday Gift Guide: presents worth giving, traditions worth keeping, and thoughtfully curated treasures for everyone on your list.