Old friends are the best friends. They’re kind—and they’re candid. They know how to turn your foibles into fortes with a gentle prod—or a cattle prod. And if, once in a while, you or they feel taken for granted— well, isn’t that the point?

That was certainly the case for the fin-du-fin designer Billy Cotton and a longtime-friend-turned-longtime-client. Having worked together on projects for over 15 years, they thought they knew each other from floor wax to façade. Over the last decade, Cotton had helped her here and there with the little Colonial Revival gem in Southport, Connecticut where she had lived with her family (husband, two daughters, one son), but they had never made it official with a full-blown house project.

Then, it happened. A sterling, significant Greek Revival house that she had mooned over for years came on the market; it was just the right size, with twin two-floor ells added in the 1930s, and about as well-preserved as a two-century-old house could be. And it was in the perfect location: front and center on one of the town’s best-preserved and most charming streets, the pillars and pediment peering straight down to the harbor’s edge. The client jumped on it, closed on it, and made a call to Cotton.

Here’s the thing: The house, in its quiet grandeur, was not quite in turnkey condition, but it was close. While the client knew that a top-to-toe renovation would be great, she was more concerned with creating a place where her kids weren’t afraid to sit and play or work or doodle or dawdle, anywhere, at any time. She wanted to put her children’s experience in the house first– a sentiment seldom heard in echelons such as hers. So instead of an eight-course upgrade from the family’s former house, she intended to keep things simple, with furniture and fabric that her kids could feel free to destroy however and whenever the fates allowed.

Caring and concerned friend that he is, Cotton leapt in and staged a design intervention. “Of course I loved her desire for the house feeling welcoming to the kids,” says Cotton. “But what I didn’t love was the idea that here she was moving with her family into this incredible house, this dream house, and there was nothing in her plan for her and her husband, nothing adult. And she’d somehow formed this bias that everything I’d show her that looked elegant was too precious.”

Slowly, Cotton was able to pry his client away from her style denial by demonstrating that an eclectic olio of furniture and finish would create a quietly chaotic, natural elegance while firmly showing the dreaded “precious” the door. His point is perfectly made the moment the front door opens: Atop a 1920s-style marble floor is a 19th-century Russian chest, above which are a pair of cast-iron urn planters from John Derian holding asparagus ferns, on top of which is a ballpoint scribble by Il Lee, across from which is a fuzzy 1970s-style Arcari runner going up the stairs, over which is a 1930s French crystal chandelier that—beautifully and wonderfully—”just doesn’t go.”

A tour of the house sees this principle on repeat. None of it really “goes,” in the old sense of the word. But what Cotton’s gallimaufry does instead is create a playful sense of adult luxury that even the children can appreciate. And while there’s a strong sense of originality to the place, few things here are so unique that they couldn’t be replaced (or at least re-covered) after meeting murder by 10-year-old.

That said, Cotton is also quick to point out that this intervention was a two-way street. “I came to this wanting her to have an incredible house in Southport, and I brought all my visions for what I wanted this to be,” says the New York designer. “And she vetoed every idea, over and over and over. And though it was frustrating at first, she really chilled me out, and she helped me start thinking of different ways this could work.”

The outsize Japanese lanterns in the living room are a perfect example. Cotton installed them as a stop-gap so the couple could move in while Cotton found better light fixtures. Two years later, they’re still there and everyone loves them. And there were trade-offs, too. Cotton scored a win with the custom-made patterned curtains he had wanted for the downstairs windows; the client succeeded in getting the stainless-steel rope swing she wanted.

In the light, fresh beauty of photographs, the house does look like a serenely chic setting fully worthy of Cotton’s reputation. But if you go visit the house on most any day of the year, you will see a living room carpet festooned (or perhaps littered) with toys.

The best part? None of it goes.

THIS STORY ORIGINALLY APPEARED IN THE SUMMER 2022 ISSUE OF FREDERIC. CLICK HERE TO SUBSCRIBE!