Tommy Hilfiger is on a Palm Beach property spending spree. The legendary fashion designer, along with his wife, the handbag designer Dee Ocleppo, have splurged on two splashy Palm Beach properties.

Earlier this month, the couple plunked down $21 million for a massive waterfront estate through a corporate entity, according to The Real Deal. Christian Angle with Christian Angle Real Estate represented both the buyer and the seller.

The mansion, built in 2006, was initially offered at $21.5 million last year, and the couple managed to score a small discount.

With three bedrooms, four full bathrooms, and three half-bathrooms, on 5,000 square feet, the home features high ceilings and “rich finishes throughout,” the listing notes.

A columned courtyard with a fountain opens to the main entrance. Multiple living areas offer wood-beam ceilings, fireplaces, and arched doorways.  

The spacious abode, described as an “in-town” Mediterranean, includes a formal dining room, as well as an outdoor dining area. The kitchen includes two islands and has access outside.

A large master suite includes a sitting area with a fireplace and a private balcony. The enormous en suite bathroom with dual vanities also opens outside.

Set on the Intracoastal Waterway, the grounds, on one-third of an acre, feature grassy lawns, a tiled pool with lake views, and a putting green.

Interior details include elaborate chandeliers and dark wood finishes, many of which will probably be replaced with a Hilfiger-style makeover. The fashion-forward couple have also put their skills into home decor, buying, remodeling, and then often selling the finished project, only to move on to the next.

In March, the designing duo picked up another plush Palm Beach property for $9 million. Perhaps the brand-new build will serve as their Palm Beach living quarters, while they make over their recently acquired waterfront mansion. The home purchased in March is similar in size, with three bedrooms, 4.5 bathrooms, and about 5,000 square feet of living space.

The couple now seem to be favoring Palm Beach after owning a home in the Miami area. 

They created an opulent, vivid-hued abode in Golden Beach, FL, as a showcase for their pop art collection. Purchased in 2013 for $17.25 million, and then completely redone, the home landed on the cover of Architectural Digest. However, the custom interiors turned out to be a tougher sell to potential buyers when they placed it on the market in $27.5 million in 2017, then quickly dropped the price to $25.9 million later that year. The oceanfront home finally sold in 2020 for $24.5 million, the Real Deal notes.

Ready to relocate to Florida, the couple also let go of their Greenwich, CT, mansion, which was built in 1939. Hilfiger had purchased the property in 2010 for a little over $31 million and proceeded to give it a total makeover.

The gated estate with over 22 acres includes a main house, guesthouse, pool, and tennis court. Offered at $47.5 million, the palatial property sold in January 2021 for $45 million.

And after his Plaza Hotel penthouse had been about 11 years on and off the market, the fashion mogul finally sold it for $31.25 million in 2019, well under the $80 million he’d initially hope to score. It was still higher than the $25.5 million that the couple spent on two units that they—naturally—combined and renovated.

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