Inside The $50 Million Tommy Hilfiger Plaza Hotel Penthouse


The founder of the renowned Tommy Hilfiger brand owned a $50 million penthouse in the Plaza Hotel that features stunning touches of him and his wife Dee Ocleppo.

Thomas Jacob Hilfiger did not find instant success from his first business which was a chain of jeans and fashion stores called People’s Place in Cape Cod, Massachusetts, that sold clothes from New York City. The business filed for bankruptcy for good as it gave birth to the Tommy Hill brand in 1979. By 1985, Hilfiger launched his line under Tommy Hilfiger Corporation, and within a few years, the company had 1,400 stores around the globe. 


The massive success has helped the company appreciate its worth to $3 billion and has gained Thomas a $450 million net worth. With so much money to play with, Thomas’ real estate portfolio includes homes in Florida, Connecticut, Greenwich, and New York City, and it’s not surprising for the fashion designer to buy, decorate, and sell his properties. Among his portfolio of expensive real estate, is the Plaza hotel penthouse on Fifth Avenue, New York. It’s special because of the beautiful interior envisioned by him and his wife Dee Ocleppo.

Remarkable History


The Plaza Hotel is located in one of the prime locations in New York City. The setting has been featured in some of the most iconic movies such as Home Alone 2 and it has accommodated top-tier persons including kings, presidents, and A-listers. The Plaza Hotel is prestigious and one of the most celebrated hotels in America. There’s a saying “Nothing unimportant ever happens at The Plaza.” The hotel’s remarkable legacy dates back to 1907. It was the dream of three men, a financier, a hotelier, and the President of the Fuller Construction Company who spent $12 million to transform a small, old hotel that was under the same name into a 19 story tower. The hotel was designed by Henry Janeway Hardenbergh, who also designed the Dakota apartments, the Willard Hotel in Washington, D.C., and The Fairmont Copley Plaza in Boston. He put out all his talents and experience into enhancing the pomp, glory, and opulence of the hotel.

The Living Room

The Hilfiger’s purchased two units in 2008 and requested the developer to merge the two, which makes it span across 6000 sq-ft, according to Town & Country Mag. The duplex has also been home to some of the appreciated celebrities such as Marilyn Monroe, The Rolling Stones, and the Beatles. Another reason that makes this apartment so special is the stunning views of the Big Apple from every corner of the house. Hilfiger paid a hefty price tag of $25.5 million to purchase the property and spent another $20 million to renovate the duplex with their personal touches. rocketing the price to $50 million.

The Hilfiger Touches To The Interior


The Staircase That Leads To The Upper Floor

As you enter the penthouse, you’ll see a foyer that leads straight to the living hall that secures a two-toned portrait of Elizabeth Taylor, two white leather couches and staked bookshelves give a comforting atmosphere. The home features one of the two domes in the building, converted into a Tea Room by the Hilfigers. According to Mansion Global, the family commissioned Henry Knight, the illustrator of the Eloise books, to hand-paint a mural for the room. The Dome Room leads to the Dining Area on the lower level of the apartment with a stocked bar area. The home features a bistro-inspired kitchen with gold hardware and aluminum tray ceilings.

The Dome Room.


There are four bedrooms on the top floor and are decorated to align with different themes.

The Nautical Themed Bedroom

Hilfiger’s younger son’s room has a nautical theme and includes a Boat-shaped bed, a nautical-themed chandelier, and other accessories. The room is in the shades of red, navy blue, white, which are also the colors of the iconic brand.

The Lavender Themed Bedroom

Next is the daughter’s room that follows a Lavender Fields theme as everything in the room hues of lavender. The room features a comfortable couch and study desk.

The Guest Room

The Guest Room has a Rock ‘n Roll theme and is decorated in shades of black and white.

The Master Suite

Speaking about the master suite and the biggest room in the house is decorated with the hues of gold and white. It’s reported that there is also a minibar and coffee cabinet close to the spacious bed to provide maximum convenience to anyone staying in the room while gazing at the stunning Central Park views.  


The Walk-In Closet

The couple gets their own space with separate closets and dressing rooms. The spa-inspired bathroom comes with separate sinks as well.

The Spa-Inspired Bathroom
The Terrace Off The Master Bedroom

Our favorite location inside the penthouse is Tommy Hilfiger’s office room. Located on the lower floor, it’s a cozy little room that shelters several bookshelves in every direction. It also houses some of the precious collectibles owned by Tommy. This includes one of the original New York Times signs, which used to be located on 43rd Street. It was bought specifically for the room, as stated by Hilfiger during his Architectural Digest Tour.

Mr. Hilfiger’s Office

Hilfiger has also kept the most iconic gifts that he received from some of his famous friends. The entrance of his office features three framed pictures which were a gift from Mick Jagger of The Rolling Stones, and the bookshelf holds some special books gifted by Karl Lagerfeld. Behind the desk, Hilfiger has displayed a Charles Wiggins painting, a gift from his wife, Dee. Lastly, the room has pictures of cherished memories captured by Annie Lebovitz.

What would be Hilfiger’s next iconic property?


View Over The Dome

From the time you enter the penthouse, there is a lot of things in every direction that pleases your eyes. From the stunning views of New York City to the elegant furniture and fittings, the penthouse is meticulously designed to squeeze out every feel of elegance. However, the Hilfiger’s moved out of New York City and sold this magnificent piece of real estate to an auto tycoon in October 2019. It was initially listed for $80 million and since it remained unsold, they dropped the price to $50 million. Since Hilfiger is in the game of flipping real estate, we wonder what his next iconic property with his personal touches would be.

Photos: TRAVIS MARK | Getty

Sources: Town And Country MagMansion GlobalMr. Good LifeArchitectural Digest


The Dining Room


The Kitchen
The Upper Floor


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