Anna Wintour, the editor of Vogue and global editorial director of Condé Nast, has been the maestro of every Met Gala since 1999. But this time, it’s personal.

Not just because the exhibition the party honors is devoted to the work of the much celebrated designer Karl Lagerfeld, who died in 2019, but because Mr. Lagerfeld was one of Ms. Wintour’s closest friends for decades. He created the clothes that, she said, “I’ve worn to the most important events in my life — to my wedding, to my children’s weddings, to Met Galas and state dinners and tennis championships at which I watched my heroes compete for their dreams.”

For her, she said, Mr. Lagerfeld’s designs were “a uniform, a kind of armor and a way of holding certain moods and memories close. His fashion does for me what fashion should. It makes me feel more confident in being myself.”

Now, when she wears his work, she said, “I still feel that I have him near.” The Times asked Ms. Wintour to pick some of the favorite Lagerfeld designs that still hang in her closet and describe the memories they evoke.

‘I don’t remember when or where I first met Karl, or what I was wearing.’

The AmfAR Gala Dress

I wore this collaged Chanel dress to the amfAR gala in New York alongside Hillary Clinton when she was in the middle of her first term as senator in 2003. I wanted to feel both chic and confident. I was delighted when, some years later, my daughter-in-law, Elizabeth, wore the same dress to her first Met Gala. Karl, who liked to strike a pose against nostalgia, took one look at her and said, “Recycled!” In fact, Karl’s dresses are enthusiastically recycled in my family, treated with reverence — but not too much. My daughter, Bee, is planning on wearing this dress to a Met after-party this year.

Honestly, I don’t remember when or where I first met Karl, or what I was wearing. I was probably nervous, because I was always nervous meeting people in the early years of my career. What’s certain is that he quickly put me at ease. He loved meeting people, and he loved to talk. We were both masters of compartmentalization — we kept our working lives quite separate from our friendship — and when we met socially, fashion was never our subject.

Karl was interested in so much else and seemed eager to escape the snow globe of his public life. In public, he embraced his image as the high priest of chic and surfaces and whatever was absolutely new. In private — a side he guarded far more carefully — he was different.

‘Karl’s dresses are enthusiastically recycled in my family.’

The Paint Box Dress

I first wore this paint box dress, inspired by the colored paints and pencils that Karl always kept scattered across his desk, to a fantastically over-the-top Chanel extravaganza that he arranged in Dallas a decade ago, one of the first such runway productions in unlikely locations. (This “traveling” model for fashion shows, breaking away from the staid runways in Paris or Milan, was enormously influential because Karl did it. Other houses soon followed.) This event was complete with a drive-in movie theater, a bucking-bronco ride and a rodeo.

Since then, that paint box dress has been to many tamer parties in our family, including my son Charlie’s wedding. Bee has also worn it to possibly too many of the weddings of her friends.

‘We’d exchange a few words or a text or two, and from these Karl was able to draw what would be just right.’

The Trompe L’oeil Dress

Karl’s dresses don’t seem to age or date to a specific era. They stay with us as we cross time and live our different lives. This trompe l’oeil dress, a homage to Coco Chanel’s love of jewelry, was part of Karl’s first Chanel couture collection in 1983. It had been in my closet for a good long time before I found the perfect occasion to wear it at President Biden’s state dinner for Emmanuel Macron.

Over the years, Karl designed some dresses specially for me, but we never talked about what these should be. It was more like osmosis. We’d exchange a few words or a text or two about an occasion, and from these Karl was able to draw what would be just right — for the event but also for me. He absorbed a lot more from people than he showed.

However broad his own interests, he always seemed to have room for other people’s, and over the years he sent me vintage prints in honor of my love of tennis and porcelain. Karl didn’t play tennis, and he didn’t care for porcelain the way I did, but it was his quiet way of being attuned to other people’s minds.

‘In the early days of our friendship we would meet at the Café de Flore, where Karl was a habitué.’

The Feather Skirt

Karl was always sending me sketches that he could create in an instant but might just as quickly ball up and toss away. One of them shows us on the dance floor, a memento of the ways we used to spend our time together in Paris. In the early days of our friendship we would meet at the Café de Flore, where Karl was a habitué. Later, he’d take me to chaotically planned, totally glamorous dinners at his house, and those incredible nights often ended with dancing.

Karl was a great dancer, and a greater night owl. As we got older and wiser and outwardly more respectable, we gave up the late nights and the Café de Flore, and I persuaded him to meet me for dinner at my hotel (Karl was perpetually, sometimes preposterously, late, and this way I found I could get some work done while I waited for him to show up). But the feathery skirt from that sketch, both ethereal and down to earth, is a reminder of that era of late-night dancing.

When one of his late parties ended, he would go home and, alone, read Hegel and sketch deep into the night. He sent me books constantly, in volume — strange, unexpected books of the kind known only to people who spend time prowling the backs of shops.

Once I was supposed to fly across the Atlantic to present him with an award in London. I’m not wonderful at adjusting to time differences, and I don’t particularly like public speaking. I am always early — in this case arriving two days in advance — and on the day of the event, a few hours before it began, I got a vaguely alarming text: Karl was just taking off from Paris. A couple of hours later, another one: Karl had landed and was in the car, but had stopped off at a bookshop.

About an hour before the presentation, there was a third: Karl is on his way but wanted to visit a gallery. Finally, within seconds of our curtain call, Karl burst into the wings with an entourage of 15 and his usual surprised “Am I late?” We were swept onstage.

‘His favorite dress on me.’

The Gold Trompe L’oeil Dress

Karl’s Chanel suits put me in mind of his dogged, unexpected strength. They are uniform and armor, a testament to slow and controlled change, but there’s something vividly human in them, too. When we went together to the 2014 opening of the Foundation Louis Vuitton in Paris, Karl told me that my gold trompe l’oeil dress was his favorite on me of any piece I’d worn. Since then, I’ve worn it many times. It’s Karl at his finest: the classic profile made new, the sparkle and simplicity, the way it puts forward an idea of strength in femininity.

Karl frequently surprised the world as a designer (he loved to turn heads), but it was as a friend that he surprised me most. Many years ago, when I was facing my first summer vacation with my children after my divorce, I was frozen. I wanted to show them a good time, but I felt in pieces. It was Karl, of all people, who sensed this and swooped in to lend a hand.

He had a vacation house in Europe, by the beach, he told us, and we should spend some time there. When we arrived, to my surprise, he’d planned a whole summer camp’s worth of activities for my young children — surfing lessons on the beach, day trips to the nearby art museum, dancing after dinner in the evenings. Karl was perhaps even less a kid person than he was a porcelain person, but he went all out when I most needed it. That isn’t something you forget. A real relationship with Karl was an association and connection built incrementally, over years.

‘I wore a lot of short skirts at the time, but none more happily.’

The Short Skirt Suit

Karl could be serious, but I’ll remember his tremendous sense of fun. In the early 1990s he designed a lot of very short skirts. We photographed a spread of them in Vogue, and I kept wondering whether the skirts were short enough. Whether in consideration of this question, or simply as a way of teasing me, he sent me a short skirt suit of my own. I wore a lot of short skirts at the time, but none more happily than his.

Or there was the benefit Chanel staged in the meatpacking district in 1991, when the uptown crowd descended to West 12th Street in an endless array of buckled leather and ruffled tulle, all of it Chanel. I remember a journalist asking him if he had ever seen so many middle-aged women in biker jackets and miniskirts. Karl’s reply was quintessential Karl, generous and coolly deadpan: “As far as I’m concerned there are no middle-aged women.”

‘He was always looking ahead to the next thing.’

The Poppy Met Dress

I never wholly figured out his contradictions. He was someone who could be rigorous in his diet, which was notoriously stringent and health-minded, and then consume a tsunami of Diet Coke. He had his love of books and magazines and printed matter but also needed the very latest technology and devices at his fingertips. He was always looking ahead to the next thing, to the future — with a fear, I always felt, of falling behind, of being caught out.

He would have been alarmed to find himself the subject of an exhibition at the Metropolitan Museum of Art. But “A Line of Beauty” is an appreciation and embodiment of his genius. Since 2005, I have worn his dresses to almost every opening gala for the Costume Institute that I have co-hosted. This poppy dress, which I wore to the “China: Through the Looking Glass” show in 2015, was an example of Karl’s dexterity and quick wits at his desk. On the runway, it was short, but, with a sweep of his pencil, it became ankle-length — and it worked beautifully that way.

Our friendship meant everything to me, and I miss him deeply. I am grateful for all the moments, such as this one, that can bring his work to life and, in the process, keep him near.