I ’m sitting in a suite at the Aman hotel in New York talking belly rings with Dee Ocleppo Hilfiger. “I never got a tattoo, but I decided that I was going to be rebellious and get a belly ring,” she says. “There’s still a little hole there.” I tell her I also went through the belly ring stage. She might be one of the most stylish women in America – and married to fashion icon Tommy Hilfiger – but she’s also the kind of woman who you can chat to about anything.
We move from belly rings to babies. There are seven children in total in the blended Hilfiger clan. “Every decade of parenting is challenging. Every decade is rewarding,” she says. “Kids grow up into young adults, but you’re always the parent. I do the best that I can. There’s no handbook on being a parent.”
At 57, Hilfiger is many things in addition to being a mother. Glamorous. Yes. Stylish. Unbelievably so. She’s also a designer – her luxury accessories brand, Dee Ocleppo, is synonymous with sophistication. Plus, she is creative director of cult accessories label Judith Leiber, known for its quirky, jewel-encrusted bags inspired by pop culture .
Working has always been important to Hilfiger, who began her career as a model before moving into fashion design in 2012. “Working gives you a sense of self-esteem. I’ll always encourage girls to pursue careers,” she says.
And while she’s married to a man who has built one of the world’s most iconic fashion brands – and remains its principal designer after nearly 40 years – her own creativity is also in full swing, including her innate knack for styling extraordinary house interiors.
“Tommy and I have bought and sold so many houses,” she says of their myriad renovation projects: a 12-room penthouse at the Plaza Hotel in New York; an 8.9 hectare French Normandy-esque estate in Connecticut; a waterfront villa in Florida. “Every project is different,” says Hilfiger. “We base the design on the style of the house, first of all, and the location.”
With their home on the private Caribbean island of Mustique, simplicity is key. “We have a lot of furniture with slick covers,” she explains. “We constantly change out all the lampshades in the house because it ’s right on the ocean, so things rust. We don ’t have anything too precious. It ’s a family home and we also rent it a lot. I would describe it as a chic but user-friendly type of home where nothing ’s too precious or expensive. It ’s designed to walk through with sandy feet.”
While her homes might be grand, she’s personally attracted to smaller, more intimate spaces. “In a lot of our houses, the rooms that have drawn me in are usually the smallest room in the house,” she says. “I like the little cosy nooks.” Hilfiger’s journey into the world of interiors began early.
As a girl, she’d take great care cleaning and organising her bedroom, describing it as “cream tones and very serene and soft. It was probably more minimal in style.” This early inclination for creating soothing spaces has evolved into a design sensibility that balances aesthetics with functionality. “I need to feel comfortable, and I love to be surrounded by things that are comforting to me or that I feel are beautiful .”
Given how many hats Hilfiger wears at any one moment, calming, tranquil spaces to retreat to are key. “I ’m not going to say that I have the secret to managing overwhelm, because I don ’t. But , for me, having gratitude is key. I ’m grateful to have all these opportunities, I ’m grateful to be busy. I also have a team of people around me that I trust,” she says. One thing’s certain: any space Hilfiger works her magic on – from houses to accessories – is bound to be beautiful.
The house sits on the shores of Mustique’s L’Ansecoy Bay and is named Palm Beach for the trees that surround it. Photographer: Kate Martin
This article originally appeared in Issue 10 of marie claire Lifestyle.
