princess diana first visit to new york

Inside Princess Diana’s Love Affair with New York City

Where she went, who she saw, what she did—and what last season of The Crown left out.

Ahead of Prince Harry's trip to New York, we're resurfacing this story from 2020 about Princess Diana's love of the city.

In the final episode of The Crown ’s fourth season, we see young Princess Diana ( played by Emma Corrin ) take on one of the highest-stakes assignments of her royal career: a packed three-day trip to New York, her first solo engagement. As depicted in the series, the visit was a coup. Diana’s empathy and glamour were on full display in equal measure, and Americans flocked to catch a glimpse of her. “She’s perfect!” a young man tells a news reporter. And, alluding to Diana and Charles’s marital issues, “If they don’t want her there, we would love to have her here.”

The reality of Diana’s February 1989 visit was pretty much the same. New Yorkers clamored for tickets to a charity gala in order to be in her presence and were moved by images of her visiting sick children. The trip was the beginning of what would become a substantial relationship between Princess Diana and the city. She would come back for high profile events like the CFDA awards, she eventually held the famed charity auction of her dresses at Christie’s Park Avenue headquarters, and she developed deep friendships with prominent residents like Harper’s Bazaar editor Liz Tilberis.

One wonders what would have been in store for Diana in New York City if she’d had more time. It’s easy to imagine any number of trips for fashion shows, Broadway binges, or black tie affairs, or even to think of an entire second act for her across the pond. She wouldn’t have been alone in her affection for New York. After all, the city holds a special allure for royals. The Duke and Duchess of Windsor found a safe haven there after his abdication, and more recently Meghan Markle retreated from the pressures of Windsor Palace to join friends for a 2019 baby shower at the Mark hotel.

Diana’s visit came about because of her patronage of the Welsh Opera. At the time, the Brooklyn Academy of Music was putting together its first season of opera, and the inaugural performance would host the Welsh company for a production of Falstaff and a gala reception . “A guy named Brian McMaster ran [the opera],” former BAM president Karen Brooks Hopkins recalls. “He and I were discussing fundraising. I said, ‘Wow, if you could only get the queen, we could really raise a lot of money.’ He said, ‘I can do better than the queen: Diana.’ I said, ‘Go for it, baby.’”

Brooks Hopkins and gala co-chair Beth Rudin DeWoody saw the $2,000 tickets sell out just on the word of Diana’s attendance. (The only person who was slow to pay up, Rudin DeWoody says, was Donald Trump.) “There are a lot of preparations when you’re hosting a princess. We had every security detail in the history of mankind,” Brooks Hopkins says. “When a princess moves, a lot of people are involved.” The co-chairs traveled to London to discuss preparations with Diana’s staff and were schooled in the ins and outs of royal protocol, which included security, what food could and could not be served, and how to approach the princess.

Readying BAM meant installing metal detectors and welcoming bomb sniffing dogs. Writing about the night, Brooks Hopkins has recalled that Groups like Committee for Legal Justice in Northern Ireland and the Irish Northern Aid Committee planned to picket the event, and 500 balloons meant to decorate the champagne reception got the kibosh by the State Department. (A balloon popping sounds too much like gunfire for comfort.) The seating arrangements required numerous hours and military precision.

diana, princess of wales wears a dress designed by victor ed

On the big night the princess appeared at BAM at 6:15 p.m. wearing an ivory sequined gown, and she was escorted to a pre-performance reception before the opera itself. “Everyone’s in black, and she enters her royal box, which we had beautifully decorated with all these greens and so forth, and she’s wearing white. Kind of a gasp goes up from the crowd, because of her beauty and the fashion of it all,” Brooks Hopkins says. Diana attended a champagne receptions at intermission and sat through the lengthy opera. After the performance, a motorcade transported her from Brooklyn to downtown Manhattan for a seated dinner for 850 at the Winter Garden. Guests included Mayor Ed Koch and Bianca Jagger.

Diana had ascended the performance venue steps on the arms of Brian McMaster and Harvey Lichtenstein of BAM. Rudin DeWoody found herself seated at a table with the princess. “We chatted a little bit. We were talking about our kids,” she says. “I remember she was obviously jetlagged and she also had to sit through this long opera. The first thing she did was grab the baguette at the table and start eating voraciously. Of course, there were lots of rules about what could go in her food or not. There’s no garlic, no onion, whatever.”

The success of the gala transformed BAM, which at the time was an emerging organization that couldn’t necessarily count on the attention of many of New York’s major arts philanthropists. “It was one of those nights when you remember every single thing that happened, even all these years later,” Brooks Hopkins says. “Really, for BAM it put us on the map. Everyone wanted to be there. Celebrities, wealthy people that we had never had access to before, all the great New York families. It was just one of those amazing nights.”

In 1989, Verona Middleton-Jeter was the chief administrator of homeless transitional housing at Henry Street Settlement, a Lower East Side social services organization. She ran a self-help program that employed women who had gone through Henry Street’s programs for homelessness or domestic violence. “These women were really proud to be given a chance, and they became one of the major advocates for homeless women with families and domestic violence,” Middleton-Jeter says. Weeks before Diana’s visit, when Middleton-Jeter was told by Henry Street’s executive director that the settlement might be one of the stops on the princess’s trip, she was skeptical. “He was like, ‘Verona, do it! Let's do it for Henry Street.’ I said, ‘Okay, if that’s what we’re doing it for. We’ll be clear we’re doing it to get Henry Street more exposure. I don’t really expect Princess Diana to do anything to help homeless people get jobs,’” she recalls.

Henry Street’s staff and residents were outside waiting when Diana got out of the car. “I walked over to the car and did exactly what I wasn’t supposed to do, shake her hand. She got out and she said, ‘Hey, we’re wearing the same colors,’” says Middleton-Jeter. “And that was that. She was just so down to earth. I didn’t have time to get nervous. So she just cut through all my anxiety.”

epfccd princess diana visits day nursery in new york, during visit to the us, 2nd february 1989

Middleton-Jeter had arranged for members of the self-help group to speak with the princess. One woman, Shirley, was particularly excited. “She just so loved Princess Di and was so happy to be a part of the group to meet her. Shirley looked at her and said, ‘Oh my God. But you’re so pretty!’ Well, I thought I would die!” Middleton-Jeter says. “We had all said, ‘Look, we got to be this way, that way.’ When Shirley looked at her and said that, I just laughed. That’s the picture that went viral.”

The women in the group and some of the residents were able to speak with Diana. She sat on the bed of a young boy and asked him about a poster he had put up. Middleton-Jeter describes her speaking naturally with the residents and showing a high level of interest in domestic violence issues. “When she went over to the daycare center, she really seemed to get into the children there. It was another opportunity to show her concern and interact with people, but in a very non-pretentious way. We were all amazed,” she says.

When Diana emerged onto the street, she was met by a massive crowd of well-wishers. Barriers were set up to keep the throngs away, and the princess was guided by her security guards. “As they would be trying to keep her away from the crowd, the whole Lower East Side was just so excited that she was there. She would go outside of where they wanted her to go to say hi to a kid. There was one little girl that had tulips, and Diana just broke the line and went to this kid and said hi,” Middleton-Jeter says.

Later that day Diana would make a stop at F.A.O. Schwarz for a lunch to celebrate British-made toys. On her final day in New York, she went to Harlem Hospital, where she visited children with AIDS. She cradled a seven-year-old boy and spoke with doctors about the disease. “Our own royalty, whatever that is, being a democracy or a republic or whatever, have not done anything nearly so symbolic as these things you are doing today,” she was told by Dr. Margaret Heagarty, the Los Angeles Times reported at the time.

Having dipped her toe into the New York water in an official capacity, Diana was able to return to the city for personal visits that allowed her to flourish. After her 1992 separation from Prince Charles, her affinity for New York only grew. In January 1995, Liz Tilberis was honored by the CFDA with an award for editorial achievement. The princess flew to New York on the Concorde to present her friend with the prize at the New York State Theater in Lincoln Center, her close-fitting Catherine Walker gown and slicked-back hair making headlines.

Designer Stan Herman was president of the CFDA at the time. “She was probably physically at the zenith of her look. I mean, the slicked-back gold locks that looked so sleek you could run your hand through them forever. The dress, the shy look that she carried with her everywhere,” he recalls. “The fun thing was the receiving line, because everybody, everybody wanted to be on the goddamn receiving line. It was impossible. I wasn’t even sure I was going to get on the receiving line… She made the CFDA gala spectacular just by her presence.”

diana, princess of wales, with her friend lucia flecha de li

Her frequent trips to New York were marked by stays at the Carlyle and visits with such friends as designer Marguerite Littman, Lana Marks, and Lucia Flecha de Lima. In 1997, she joined Tina Brown for lunch at the Four Seasons—the only time Diana ate there, according to Julian Niccolini, co-owner at the time. “When she walked into the room, because she walked in by herself first, it was reminiscent of the day that Jackie Onassis came in for the first time. The entire dining room stopped,” he says. “Most of these people were Wall Street guys, lawyers, real estate tycoons. They just couldn’t believe how beautiful, how great-looking this particular woman was. It was quite a moment.” Diana wore a green Chanel suit. It was the last meal the friends would share.

What would end up being the princess’s highest-profile event was the 1997 auction of her dresses at Christie’s. Per the suggestion of her son William, Diana sold 79 of her most famous gowns at the auction house to benefit the Royal Marsden Hospital Cancer Fund and the AIDS Crisis Trust, which Littman had founded. The sale raised $3.25 million.

council of fashion designers of america awards ceremony the princess of wales new york

Chef and author Alex Hitz became friends with Diana through Littman. “Diana said to Marguerite, ‘I’m going to give you my dresses.’ And Marguerite said, ‘Oh my God, do I dress that badly?’ But what she meant was she was going to have them auctioned off for Marguerite’s charity.” He remembers the days leading up to the auction as a nonstop flurry of activity. “When they came to New York to sell the dresses, it was a weeklong thing. Lollapalooza of Diana and all the dinners and all the parties. We were all at the Carlyle together,” he says.

For Nancy Valentino, a Christie’s staffer who was on the team that organized the sale, the night will never be forgotten. “As staffers, we had protocol meetings. You know, ‘Don't approach, stay still, look down,’ or whatever. And up the stairs comes this luminous, amazing, sort of angelic, beautiful person... When you saw her, when you were in her presence, you knew you were in the presence of someone who was extraordinary,” she says. “She was warm and friendly, looked everyone in the eye and thanked them.” It was her final visit to a city that she loved so much, and which clearly loved her back. Two months later she would be gone.