Katie Holmes and Joshua Jackson Reunite and Chat All Night at Brunello Cucinelli Event | Vanity Fair

16 April 2026 2546

Twenty minutes before Brunello Cucinelli’s New York screening of Brunello: The Gracious Visionary, I still wasn’t dressed. This wasn’t ideal. “Screening” doesn’t quite describe the full scope of the Italian fashion designer’s event: In addition to a showing of the film, there were cocktails and a black-tie gala dinner—all held at Lincoln Center, the monumental performing arts center that’s served as the beautiful beating heart of Manhattan’s culture since its first theater opened in 1962.

I still wasn’t dressed because the black-tie dress I’d wanted to wear—simple, silk, floor-length—hadn’t made it back from the dry cleaner in time. So I found myself staring at three options in my closet: a knee-length black dress, a floor-length black dress, and a chartreuse patterned set. All of them were wrong. The first violated the dress code. The second I hadn’t gotten tailored yet, so the too-long hem dragged on the floor. And the third? Very flamboyant. Which for this was just…so wrong.

You don’t need to be a fashion fanatic to know the world of Brunello Cucinelli. In fact, you could have a keen understanding even while holding only a tangential interest in style: Brunello Cucinelli is a publicly traded, extremely profitable Italian fashion brand with over 130 boutiques worldwide. It was the keystone species of the most dominant trend of our era, stealth wealth. Men, women, and kids (fancy kids) all wear the designer’s clothes. As a result, his aesthetic is keenly understood: luxurious cashmere sweaters made from the finest materials, which have earned Cucinelli the nickname King of Cashmere; impeccably tailored jackets and pants, all often in a neutral color palette or occasionally a rich, supple color; sequins used elegantly and sparingly. It also exudes, well, Italy: Brunello Cucinelli epitomizes sprezzatura, an Italian term that roughly means a studied nonchalance. Every single one of my options seemed to violate the very code on which Cucinelli had built his empire.

But I had to go.

I arrived at Lincoln Center several minutes later, in the chartreuse set. Black cars lined Columbus Avenue and, even from a distance, I could spy endless velvet ropes in front of the David H. Koch Theater. When I finally got there, there was no doubt about the cause of all the fanfare: Hanging from the Metropolitan Opera House were banners of the film poster, so large they seemed to reach the blue of the sky. Sprawled across the plaza was a beige carpet lined with black velvet ropes. Tourists nearby had gathered to watch as famous faces strolled in—including Katie Holmes and Joshua Jackson, creating an impromptu Dawson’s Creek reunion in the process.

Inside the theater was a sea of glamorous stars in neutrals. Naomi Watts, wearing black trousers and a white oxford with an untied bow tie thrown artfully around her neck, greeted Dree Hemingway, who wore a black sequined short-sleeve dress. (She wasn’t the only Love Story star in attendance: Grace Gummer was also there, wearing a white button-down tucked into a glittering champagne skirt.) Allison Williams sat nearby in a pewter gown, politely introducing herself to her neighbors. Oscar Isaac had on a classic tuxedo. In fact, the most colorful man in the room might have been Jackson, who had on a jacket in a rich currant shade.

Italians may have a reputation for running late, but not Mr. Cucinelli. He took the stage promptly to give his remarks. “In order to speak with my heart, I need to speak Italian,” he said in English, before launching into his native tongue. A translator did the rest: “I wanted to retrace the story of my life so the next generations—my children and grandchildren—could listen to my words straight from the source,” Cucinelli said. While some may have wanted to opine, Cucinelli kept it brief, speaking for just over two minutes.

For the next two hours, however, he had plenty to say in the glossy film by Giuseppe Tornatore, who also directed Cinema Paradiso. The movie began with Cucinelli’s childhood in the countryside outside Perugia, where his family had no running water, and moved on to his young adulthood, during which he scraped together a living by playing cards in a bar. (Fun fact for the reader but not-fun fact for whoever has played a game against him: Cucinelli knows how to count cards.) Eventually, it explored how he built one of the most luxurious brands in the world. It got micro too: In multiple scenes, he expressed his distaste for the color green. I sank further and further into my chair.

Afterward, dinner was underneath the gold leaf ceiling at the promenade. Ryan Seacrest made the rounds, as did Martha Stewart, who was a vision in sparkly stripes. Antoni Porowski, ever the host, offered to pour olive oil for his tablemates, who included Helena Christensen. Holmes and Jackson continued to chat away. But no one attracted more attention than one person: Cucinelli himself, who shook hand after hand while wearing his own blue tuxedo jacket. His family—including wife Federica Benda and daughters Carolina and Camilla—stayed close by the entire night.

Dinner seemed like it was airlifted from Umbria: Parma ham and Pecorino Romano cheese and bowls of buffalo mozzarella. The main course was Cucinelli’s favorite: rigatoni al pomodoro with fresh basil. A dish whose shade, while more vibrant, reminded me of my fateful dress. Despite the prevalent belief that fashion people don’t eat, every plate I saw that night was scraped clean.

At around 10:30 p.m., the journey into Cucinelli’s world came to a languid end, with guests slowly trickling out into the night. As I stepped out, I looked down at my outfit. Maybe it was time for The RealReal. I wanted to make room for something…cream.

Grace Gummer, Brunello Cucinelli, Federica Benda, and Dree Hemingway

Shonda Rhimes

Martha Stewart

Oscar Isaac

Allison Williams

Christie Brinkley

Joshua Jackson and Grace Gummer

Sarah Catherine Hook

Dree Hemingway

The crowd gathering before the screening of Brunello: The Gracious Visionary

Helena Christensen

Martha Stewart, Brunello Cucinelli, and Naomi Watts