By Eric Wilson
Updated Nov 01, 2018 @ 8:00 am
Credit: Alexander Neumann/Shotview

Name eight people you’d invite to a fantasy dinner party.

It’s a well-worn parlor game and an excellent icebreaker whenever conversation at a social event turns deadly, offering plenty of opportunities to delight, inspire, or ignite a debate. It also happens to be a favorite topic of the riotously funny designer Michael Kors, who has never been a slouch when it comes to entertaining. And so, to make things interesting for our latest designer feature, InStyle challenged him to dream up a guest list of his own, sent out the RSVPs (dress code: Michael Kors resort realness), and voilà — the next thing you know, dinner was being served in real life, along with lots of dish on the side.

VIDEO: Michael Kors Dinner Party

It happened one evening in August. Kors, at the center of a bevy of glittering swans, was dressed all in black with aviator sunglasses, perching on the back of a banquette at the Monkey Bar in Midtown Manhattan. The scene upstaged even the Jazz Age icons depicted in Ed Sorel’s murals surrounding them. There was Kors’s old friend Iman, who has known the designer for at least half of his 37-year career. She made a rare appearance, “and only for Michael,” she insists. There was the model and musician Karen Elson. And Kors fans from the world of theater, television, and film turned up too: Cynthia Erivo, Sutton Foster, and Judith Light (wearing a black sequined tuxedo she described as “gender-fluid”) were introduced in quick time to the other guests, Tiffany Haddish (who had been the designer’s date at the Tony Awards in June), Savannah Guthrie, and Naomi Watts. Few of them had met previously, but you wouldn’t have known it from all the laughter that ensued.

Credit: Alexander Neumann/Shotview

“We were just organized chaos,” says Erivo, who met Kors, an avid theatergoer, during her breathtaking run in The Color Purple on Broadway. “We all forgot there were photographs being taken.”

Credit: Alexander Neumann/Shotview

“It definitely got loud,” adds Guthrie. “It seriously was such a great group of women you fell in love with for different reasons. Sitting across from Iman was like meeting the queen.”

Credit: Alexander Neumann/Shotview

This melding of personalities, as with pretty much everything touched by the hand of Michael Kors, was entirely by design. Rule No. 1 for throwing a successful soirée, he says, is to embrace diversity, and by that he means to welcome guests of different ages, backgrounds, and professions. “If I can turn Karen Elson and Judith Light into besties, that’s fantastic,” he says. At the same time, there should be something that unites the whole group — in this case, they are women who all have a strong sense of humor about the world.

Credit: Alexander Neumann/Shotview

“Those are my favorite people to sit down at the table with,” Kors says. “When I’m designing a collection, everything I do deals with yin and yang — my clothes are practical yet indulgent — and it’s the same with the people I want to spend time with. They can be supersmart or silly.”

That combination only begins to describe what happened at the table, much of which, by agreement of all involved, does not appear here. Consider that Rule No. 2: A meal, given today’s go-go-go pace and the relentless demands of constant connectivity, should be treated as sacred. “Other than taking a picture, put your phone down so that you are able to connect,” Kors says. And try not to talk too much about work. “Even with the most stylish women in the world, I’ve never said, ‘Let’s talk about shoes!’” The conversation was so good, though, so deeply meaningful at certain points and, well, slightly profane at others, that the participants have agreed to share some details.

“We were able to go deep right away,” says Light. “Michael was the conduit for that.”

Haddish is one of the funniest women in Hollywood, and her new movie, Night School, would go on to have the highest-grossing domestic opening weekend for a comedy in 2018. Between dropping punch lines about hanging out in a gay bar (“These men take care of you. They were nurturing me, looking out for me — I was dancing all night last night, trying to get me two husbands”), she bonded with Elson and Erivo, talking about the importance of family and the sacrifice of working long hours. Kors asked about Watts’s children, one of whom is obsessed with fashion. Suddenly, Haddish and Erivo began singing a made-up song, repeating the words “about that life” until everyone at the table had joined in. And then things turned wickedly funny again, as Haddish recalled how, at the Tonys, she stole some of the roses decorating the backdrop of the step and repeat and then began throwing them at the performers onstage. “It was like watching Maria Callas at La Scala,” Kors says. “That was you!” Erivo says, remembering how the roses remained onstage for the duration of the event because the stagehands couldn’t touch them.

Credit: Alexander Neumann/Shotview

“I, of course, took it to a fashion-show moment,” Kors says. “When I was at Céline in Paris, I was at the Louvre, where a smaller show was going on, and apparently a model’s hair extensions had fallen off and were sitting on the runway until they got stuck on the heel of another model’s shoe.”

Rule No. 3 comes from Light, who recalls a dinner she once attended where the host had warned guests that he would be starting with one question addressed to the group before the conversation splintered into smaller offshoots. “It makes a difference because everyone is engaged,” she says. That night the question was, When was the first time you went to the theater? At this dinner, each guest was asked whom they would have invited. There was a surprising amount of overlap in their answers: Pretty much everyone invited the Obamas, a few requested Oprah Winfrey, and, curiously, many showed a strong interest in asking both Harry Belafonte and Lucille Ball. “This is going to be a fun party, and everybody is going to be laughing,” Haddish says.

Credit: Alexander Neumann/Shotview

This brings us to Rule No. 4: Not everything has to be fancy. Some of Kors’s favorite dinners are ones in which the host creates a relaxed experience with a simple menu. Besides, a casual environment reflects who he is as a designer, not to mention his entire aesthetic — indulgent, yes, but also relentlessly optimistic.

“The more barefoot, the better” has always been his philosophy for entertaining, he says. Kors and his husband, Lance Le Pere (the executive vice president and creative director of the women’s collection), have done things at home much the same way for more than 25 years, despite the incredible performance of Kors’s company, which has made the designer ridiculously wealthy since it went public in 2011. “I was putting the lobster rolls together myself then,” he says. “Now I might have help, but I’m not serving chateaubriand and cherries jubilee.”

Credit: Alexander Neumann/Shotview

Another suggestion from Kors is to play what he calls “runway music” to get people dancing. His recommendation is a mix of Beyoncé, Michael Jackson, Madonna, Donna Summer, and Rihanna.

For all his modesty, a few weeks after the dinner, Kors stunned the fashion world with the announcement that the company had agreed to acquire Versace for $2.1 billion while changing the corporate name to Capri Holdings. Speaking of potential dinner dates, Kors says Donatella Versace would make a welcome addition.

“She and I are both fans of tan and blond,” he says. “I told Donatella that in my South Beach days, I was known to wear head-to-toe Versace, but at this point in my life I might be able to sneak in a piece.”

This relates to Rule No. 5: Be respectful of your guests and their time. Life moves fast, so when people do show up for you, that is a gift that should be acknowledged. And most designers will tell you that their greatest thrill is not to see their clothes in a runway show but to see them worn by women in real life. Having eight of them around a table, well, that’s better than dessert.

“They always say, as a designer, you’re only as good as the women you dress,” Kors says. “And these are women who could wear anything, so to see the clothes come to life is my favorite part."

Kors’s dinner guests in Michael Kors Collection clothing and shoes and Michael Kors Collection, Michael Kors, and Michael Kors Access jewelry (worn throughout). Photography: Alexander Neumann. Styling: Julia Von Boehm Manicures: Gladys Castillo, Daria Heardman, Candice Idehen, and Jenny Valle for Starworks Artists. Production: Sisters Productions.

For more stories like this, pick up the December issue of InStyle, available on newsstands, on Amazon, and for digital download Nov. 9.