In our Packed To Perfection series, TZR follows industry tastemakers to local haunts and far-flung destinations alike to see — and shop! — what they’re wearing while out and about in the world.
Dee Ocleppo Hilfiger knows how to do it all—and dress for it. The founder, creative director, and longtime fashion fixture has built a life of impeccable taste, frequent travel, and life in the fast lane alongside legendary designer Tommy Hilfiger.
“We travel every summer to Europe, and I always look forward to Monaco where I lived for 13 years before I married my husband,” Hilfiger tells The Zoe Report. “I love catching up with old friends there over seaside dinners, and feel right at home whenever I go back.” Between annual trips to the French Riviera for F1 racing (Tommy Hilfiger has sponsored the luxury race for over 30 years) and perusing the party track throughout Capri and the Amalfi Coast, Ocleppo Hilfiger has international expeditions down to a science: “My best travel hack is about planning ahead. The destination dictates everything, and I plan each look for daytime and evening ahead of time, instead of just packing a bunch of stuff.”
Still, there are some closet mainstays that make it it in Ocleppo Hilfiger’s bag no matter what. “I always pack these five items, no matter where I am going: A great pair of jeans, a white button down shirt, a black cocktail dress, elegant black pants, and a chic trench coat,” she says.
Ahead, take a peek at Ocleppo Hilfiger’s fail-proof formula for a proper Monaco adventure.
Print Happy
Dee Ocleppo Hilfiger
“I love a matching set for the boat,” says the fashion expert. “We’re heading to lunch at the Monte-Carlo Beach Club.” With its Art Deco architecture, seawater pool, private beach, and see-and-be-seen crowd, it remains one of Monaco’s most storied summer institutions.
Lady In Red
Dee Ocleppo Hilfiger
“On the boat sunbathing. I love a bold one-piece, and this is so flattering from SKIMS. I always wear a hat on the boat, too — sun protection is real!”
Maxi Moment
Dee Ocleppo Hilfiger
“We’re having dinner on the boat this evening — such a relaxing scene. It’s one of my favorite moments to spend with family and friends, and the view is gorgeous. A simple, feminine dress and bare feet is the recipe here.”
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Dee Ocleppo Hilfiger
“When it comes to race day, I always stay on-theme with a blend of Riviera-inspired pieces, as well as graphic race accessories for a fun twist.” The Monaco Grand Prix has become one of F1’s biggest fashion moments, and a breezy dress with a flats is ideal.
Beach Scene
Dee Ocleppo Hilfiger
“Heading to lunch at La Guerite in head-to-toe Johanna Ortiz. This set is one of my favorites for leisurely days that turn into a night out.” Perched on the rocky coastline of Cap d’Ail, the glamorous outpost is beloved for its fresh menu, barefoot-luxe energy, and postcard-perfect views of the Mediterranean (and the crowd).
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