Dee Ocleppo Hilfiger's Insider Guide to Italy

Love, food, shopping and serious R&R continue to draw the iconic designer to Bel Paese.

PORTRAIT BY JOHN RUSSO | WRITTEN BY MISTY MILIOTO

Love first brought model-turned-accessories designer Dee Ocleppo Hilfiger to Italy in the 1980s, when she and her boyfriend lived just outside Milan. Almost a decade later, that boyfriend was ancient history when she married Italian tennis player Gianni Ocleppo and moved to Monte Carlo, but often traveled back to Italy; the couple divorced in 2003. Five years later, the Italophile married fashion desiger Tommy Hilfiger. Visiting the finest Italian factories with him inspired her to create a collection of accessories that combines the exceptional quality of Italian leather artisans with a distinctly American point of view. Dee Ocleppo shoes and handbags were now favored by fashionistas who want affordable luxury. These days, the entrepreneur frequently returns to the bel paese (beautiful country) for work and to visit her two eldest children, who live in Alba. Here, she shares her favorite stop along the way.

Q: Are you currently working with any Italian fashion designers?

A: I’m working with Jeremy Scott, head designer of Moschino, on a special project for Judith Leiber.

Q: Which are some of your favorite cities in Italy?

A: My favorite city to visit in Italy is Venice, because it is so unique and simply magical. It immediately transports me to another time and place, and it always feels surreal when I am there. I also adore going to Rome, Florence, Capri, Positano and Alba. I love Rome and Florence especially for their museums, shopping and architecture. I love Capri and Positano for the stunning views, beautiful waters and local artisans—especially the sandal makers. Alba is a place where my older children call home; it is the Napa Valley of Italy, with fantastic vineyards and most famously known as the home of the whitet ruffle. It’s best to visit in October and November when it is the height of truffle season. Yummy!

Q: Which hotels do you like best to stay in Italy?

A: One of my favorite hotels in Italy is the Park Hyatt Milan. I love the service, location and clean design. I also love the Hotel Danieli in Venice fora classic and traditional Venetian experience.The Il San Pietro in Positano is exquisite, andI highly recommend it for a romantic getaway.The Belmond Hotel Splendido is wonderful in Portofino for a weekend escape and [it has] the best terrace in town for drinks.

Q: What are some of your favorite shops in Italy?

A: I love the Serravalle Designer Outlet in Serravalle Scrivia [Province of Alessandria in the Piedmont region]. It is worth the trip for great bargains on everything from Gucci to Bulgari. I also love shopping in Capri when on vacation— The Sea Gull for the most beautiful and unique ceramics, Russo L’Uomo and Donna Russo for the latest and greatest designs, and the most wonderful vintage store, Wonderland, where you can find a treasure trove of the most unique items of clothing and accessories. Lastly, when I travel to Venice, I love heading to Murano to visit the glass factories where you can find the most beautiful stemware on the planet. My favorite factory is Signoretti. When I was first engaged with Tommy, we purchased our very first glasses together and had “H” engraved on them. They are still very meaningful to me today.

Q: How about favorite restaurants?

A: Lo Scoglio in Nerano [on the Amalfi Coast] is one of my very favorite restaurants in Italy. It is a family-owned seaside restaurant where everything is organically grown on their farm. Food is shared family-style and everything is just delicious. I also love Giacomo Bistrot in Milan for a casual evening and the best pasta pomodoro, as well as a great wine selection. Harry’s Bar in Venice is a classic. Bellinis are a must. I am usually full after the bread basket.

Q: Where do you go for simple relaxation?

A: For relaxation in the summertime, I highly recommend going to Sardinia. I particularly love Porto Cervo and Porto Rotondo [both in Sardinia]. The beaches are beautiful, and it is a wonderful place for relaxing and going for a gelato and evening stroll. In the fall, I love the Castello di Guarene in the Piedmont region. It isa beautiful 18th-century castle with a relaxing spa, breathtaking views, and plenty of great food and wine. The Four Seasons Hotel inFlorence is also a favorite. They have the most beautiful gardens with incredible sculptures to explore and roam during the day, as well as great service and a wonderful spa.

Q: How do like to travel within Italy?

A: I love traveling by boat for visiting the coastal cities and towns, but I also love driving through the countrysides of Tuscany and Piedmont. It is quite easy to drive from place to place in Italy.However, in the larger cities, such as Milan orRome, I would definitely recommend hiring a taxi or a private driver.

Q: What would be your perfect itinerary?

A: My perfect itinerary—if I had a month—would be to try to explore all the different regions in Italy. I would start in Portofino, then head to Milan, theTurin/Piedmont region, Venice, Bologna, Rimini, Florence, Pisa, Siena, Rome, Naples, Capri,Taormina and then Palermo. Then I would leave a few extra days for exploring smaller towns. Afterwards, I would then need to head to a weight-loss camp for another month.

Q: Can you think of three things that are quintessentially Italian?

A: Great food, finest-quality craftsmanship and the dangerously charming men.