Inside Dee Ocleppo’s Closet

“I always think about shoes,” mused Dee Ocleppo, better known as Mrs. Tommy Hilfiger, while in her private dressing quarters at the couple’s sprawling Greenwich, Conn., home. Considering the 46-year-old owns styles from the world’s top designers, a certain amount of obsession is warranted.

“I’ve never counted, but I’m definitely not in the Imelda Marcos category,” Ocleppo said of her full collection, which is split between this home and the Hilfigers’ apartment at The Plaza in New York. “I have quite a few pairs. I don’t really get rid of them. I keep them and acquire [more].”

Unsurprisingly, the footwear reflects her jet-setting lifestyle, as she spends most of her time traveling with her husband. And Ocleppo has every occasion covered, with a closet that runs the gamut from Hunter wellies and René Caovilla strappy heels to minimalist sandals.

“I love a fantasy shoe, but I also think it’s necessary to have a classic shoe like a great pump,” she said. “I’m not one of those women who walks the pavement of New York in 10-inch heels.”

Recently, Ocleppo became a designer herself, creating for HSN a line of handbags with changeable covers called Deesigns. The styles range from $100 to $150, and additional covers can be purchased for less than $50. While Ocleppo admitted she hadn’t planned to get into the biz, she’s certainly enjoyed the ride.

“People really loved the idea, and the customer responded,” she said of the line. “The price points are great, and I’m having so much fun.”

Clearly, being fashionable comes easy to the Hilfiger clan.

“We have a lot of designers in our family,” Ocleppo said. “By osmosis, we’re all always thinking about design.”

Designers featured:
Christian Louboutin, Dolce & Gabbana, Jimmy Choo, Lanvin, Manolo Blahnik, Miu Miu, Prada, Tommy Hilfiger and Yves Saint Laurent

Most beloved pairs:
“I bought two pairs of the Pradas with the wings and the lights. I scooped them up in Paris after I’d been searching for them. I also have an older pair from Prada with flowers and a sculpted heel. I love fun shoes like that.”

Best styles for the city:
“I wear ballet flats a lot for walking around the city, and then in the wintertime I’ll wear a flat boot. I will torture myself for the sake of beauty in the evening because I know I’ll be sitting half the night. But to walk around [in heels] when you know you have to walk blocks and blocks doesn’t make any sense.”

Ideal looks for the country:
“Out in Connecticut, I keep more casual styles, like my wellies and Hunter Boots.”

Preferred places to shop for shoes: “I buy a lot of my shoes at Bergdorf Goodman because it’s right next door to wear I live [in Manhattan]. And I buy shoes when I go to Europe, [in] Paris or Milan.”

Favorite pair of Tommy Hilfiger footwear: “
Tommy did a boot called the Dee that came up over the knee, so those are definitely one of my favorites.”

Front-row style:
“At Tommy’s shows, I’m normally dressed in what they’re showing, so I’ll wear a shoe that will be coming out next fall or spring. Luckily, I’m the same size as the models, but I usually have to fight for the pair I want because someone backstage says they need them for the models. I’m like, ‘I need them to go with my outfit!'”

Biggest splurge:
“It was a mistake. I walked into Manolo Blahnik, and they were having a sale. I found these black croc open-toe slingbacks, and I quickly glanced at the price tag and thought it said $400. I gave the girl my credit card, and when I went to sign, it said final sale $4,000, or something like that. I got so embarrassed about it that I just quietly signed it and walked out of the store. I was so embarrassed, I just sucked it up and thought, ‘[I’ll] wear them all the time.’ I wish I could say I wear them all the time.”

Best buy on vacation:
“I love the sandals in Capri. Every time I go back, I buy more. They’re just very simple Jackie O T-strap sandals. And if you’re more daring, you can get charms put on them.”

Least-favorite styles:
Birkenstock sandals and Ugg Australia boots. “I’ve tried them, and they are very comfortable, but I can’t do it.”

Dream shoe collaboration:
Christian Louboutin. “He does a lot of fun and creative styles. I would probably get him to put a more sensible heel on some of the shoes, although I buy them and I wear them [anyway].”

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