Tommy Hilfiger is trying to sell his Plaza Hotel penthouse at a discount.

As retailers across the country slash prices in their stores today for Black Friday, a cooling luxury property market in the U.S. has meant that many retail executives and fashion designers have had to reduce the price of the homes they’re trying to sell as well as the clothes they’re flogging.

Here, in the spirit of Black Friday, WWD rounds up the biggest multimillion-dollar property discounts among the fashion set for your perusal from the comfort of your armchair.



Now: $17.95 million

Then: $26.5 million

Discount: 32%

The former J. Crew boss and serial property investor Mickey Drexler is once again trying to sell his secluded Hamptons beach house and this time he’s seeking $17.95 million.

While this may still seem like a lot of cash to us mere mortals, it represents quite the discount from the original listing price of $26.5 million when the J. Crew chairman and former chief executive officer tried to offload it in 2015.

So what does almost $18 million buy you in the Hamptons? Perhaps unsurprisingly in the uber exclusive beach enclave that the super rich flock to every summer, it’s not a mansion, but a three-bedroom, 3,500-square-foot wooden house.

Still, it’s a pretty nice house set on more than two acres of land at the end of a private driveway with 315 feet of ocean frontage. What’s more, all bedrooms have access to the outdoors via wide wraparound decks, while a wooden boardwalk provides direct private access to the beach.

Mickey Drexler’s house backs onto Wainscott Pond.  Douglas Elliman Real Estate



Now: $50 million

Then: $80 million

Discount: 37.5%

In Manhattan, Tommy Hilfiger has been working hard to sell his tony Plaza Hotel penthouse since 2008 but hasn’t had any success despite it boasting a breakfast nook adorned in an “Eloise” mural in one of the landmark building’s four turrets, as well as a terrace that looks like a life-size chess set overlooking Central Park.

After being on and off the market several times, it’s back again with a $50 million price tag, a huge discount from the $80 million the 66-year-old fashion designer and his wife, Dee Ocleppo Hilfiger, were asking at one point.

Hilfiger previously told the Wall Street Journal that he had received a couple of offers in the past, but they didn’t come through. “One I didn’t accept and the other the guy didn’t come up with the money. I’m of the belief that if it sells, it sells,” he said. “If it doesn’t sell, I’ll just keep it.”

The library in Tommy Hilfiger’s Plaza Hotel penthouse.  Travis Mark



Now: $5.995 million

Then: $14 million

Discount: 57%

The sale is also most certainly on in Connecticut as fashion designer Alexander Julian has slashed almost $8 million off the asking price of his sprawling estate.

After several price cuts and disappearing from the market altogether, his Ridgefield, Conn., mansion is once again for sale for just under $6 million, a steep discount from when it was originally listed for sale in 2012 for a whopping $14 million.

Julian, best known for his colorful men’s wear collections and his original design of the NBA’s Charlotte Hornets uniforms, paid $1.65 million for the estate in 1988 and told “Open House NYC” in a 2013 interview that he invested “millions and millions into redoing the property.”

Set on an impressive 30 acres, the estate includes a 6,043-square-foot, five-bedroom main house, a tennis court, a swimming pool, pool house, a guest house, a greenhouse, summer cottages and a barn.

Alexander Julian’s picturesque pond.  Courtesy Photo



Now: $25 million

Then: $34 million

Discount: 26%

Back in Manhattan, Jimmy Choo cofounder Tamara Mellon is still trying to sell her Upper East Side penthouse that she first listed in the summer of 2014 with a $34 million price tag.

The former British Vogue accessories editor, who set up the famous shoe company with designer Jimmy Choo in 1996 and has since gone on to create her namesake brand of footwear, has since reduced that to $25 million, but so far that hefty price reduction has failed to entice buyers.

The five-bedroom, 7,000-square-foot penthouse, which comes with an impressive roof terrace and a large shoe closet that would make Carrie Bradshaw jealous, is on the top of the Grand Carhart building at 3 East 95th Street, which was built in 2013.

Tamara Mellon’s shoe closet.  Evan Joseph Images



Now: $19.995 million

Then: $25 million

Discount: 20%

Finally, in Malibu, Peter Koral, cofounder of Seven For All Mankind, is looking for a buyer for his $20 million Malibu beach house, which he is also advertising for rent for $150,000 a month this summer.

The jeans entrepreneur, who sold Seven For All Mankind to VF Corp. for $775 million in 2007, has been trying to sell his home on Broad Beach Road since March 2015 when it had a near $25 million price tag.

The six-bedroom, Cape Cod-style house, which comes with a distinctive red copper roof, has impressive coastline views from nearly every room. If that’s not enough, three-bedroom suites on the lower level open out to an infinity pool and spa just above the sand.

Peter Koral’s infinity pool.  Courtesy of Zillow

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