When Brooke Shields was a young model and actress in New York, she befriended some of the heavy hitters in the downtown art scene—but never had the money to actually purchase their work.

“I was surrounded by artistic people—by Andy Warhol and Keith Haring and just being in their zeitgeist,” Shields told Artnet News. “Andy came to my birthdays. I just knew that there was this incredible person and artist at my celebration, and he was lovely and sweet. If I could make Andy laugh, that was something important to me as a little girl.”

Shields’s role as an art collector came much later, after she developed a relationship with the New York Academy of Art, the private New York art school that emphasizes figurative art, and was cofounded, as it happens, by Warhol.

“Fate would have it that I ended up being a part of something that was such an integral part of what Andy wanted to do,” she said.

Brooke Shields bids on work at the New York Academy of Art’s Take Home a Nude benefit. Photo courtesy of BFA.

Since 2014, Shields has been one of the academy’s highest-profile supporters and a fixture at its annual fundraising galas. She even dipped her toe into the field of curating by helping stage presentations of alumni work for the academy at art fairs.

This year, the academy is taking a different approach to benefit events. It renamed its “Take Home a Nude” benefit, which typically features a live auction of work by students and friends of the academy, as “Artists for Artists,” an online auction of some 200 works running through October 26. A livestream benefit with appearances by Padma Lakshmi, Liev Schreiber, and Alan Cumming is being held October 20 at 6 p.m.

Shields will tune in, too—if she can get her Wifi back up and running, that is. She’s currently staying at a cabin in the remote Scottish countryside where she’s filming a Christmas rom-com co-starring Cary Elwes for Netflix. We reached Shields by phone to chat about her approach to buying art and why she’s never regretted a purchase.

Mats Gustafson, Untitled Male Nude (2014). Photo courtesy of the New York Academy of Art.

What was your first purchase and how much did you pay for it?

The first from the academy was probably in 2014, by Mats Gustasfon. It was a male nude. It’s probably one of the more expensive works that I have. The art that I purchased before that, I don’t know that it was any notable art.

I became involved with the academy by happenstance. My girlfriend BJ Topol, who is an art consultant, had introduced me to Will Cotton. My husband wanted to give me a 10-year anniversary present, so he called BJ and asked for advice. She said, “I know for a fact that she really loves Will Cotton. Why don’t you commission him to paint portraits of your girls?”

When I walked into the studio and Will unveiled these pictures, I just cried. I couldn’t believe it. We thought they were going to be just small little charcoals, and they’re big portraits! He was able to capture very different characteristics in their personalities.

Brooke Shields at a New York Academy of Art drawing party. Photo courtesy of BFA.

Later, Will invited me to sit for Take Home a Nude. I met [academy president] David Kratz because I had to change in his office (I got to wear a little slip). [Modeling for life drawing] is not an easy thing to do. What I loved about it was there were these increments of 10-minute poses—I can’t even imagine being able to capture anything on paper in just 10 minutes. It just was such an extraordinary experience.

What was your most recent purchase? 

I’m always buying stuff when the academy has auctions. One of my favorite ones is by Shiqing Deng. She’s lovely. And one by Kiki Carillo that’s a portrait of a little girl holding a tube of lipstick. She’s put the lipstick all on her face in a round circle, and she’s so proud of her herself.

In the family room, portraits of Shields alone and with her children, including images by Robert Mapplethorpe and Annie Leibovitz, are propped alongside works by Richard Avedon, Adam Fuss, and others. Photo ©William Waldron/OTTO for Architectural Digest.

Which works or artists are you hoping to add to your collection this year?

I’ve been literally in isolation out in Scotland, so I’m not sure. But I recently bought a Dina Brodsky butterfly study, and a Sara Issakharian that was really beautiful.

What is the most expensive work of art that you own?

I don’t spend a huge amount of money. I buy what I really love. The most I’ve ever spent is maybe $6,000. It’s not really about the money as much as it is about the piece. I can’t really categorize myself as someone who collects based on appreciation or price. I think it’s more about seeing a piece that registers with you. Not being someone who has any talent as an artist, I just really value it.

Shiqing Deng, Hug. Photo courtesy of the New York Academy of Art.

Where do you buy art most frequently?

I have bought most of my art at the academy. I support the school, I value the talent, and if I like it, and I want to live with it, and I can afford it, then I buy it. These are pieces that have spoken to me and they’re very eclectic.

Is there a work you regret purchasing?

I don’t think I ever regret buying an artwork. Even if I don’t want to live with it, I’ve purchased something that somebody has given their heart to, and that can’t be bad.

If you buy something because someone tells you it’s going to appreciate in value, but you don’t like it, that’s not money well spent. I’m sure most of my art won’t appreciate, but guess what? I appreciate it!

Brooke Shield’s living room, with Louis XVI–style armchairs, a French Empire commode, a 1970s Lucite-base cocktail table, a Keith Haring painting gifted by the artist, and portraits by Will Cotton of Shields’s two daughters. Photo ©William Waldron/OTTO for Architectural Digest.

What work do you have hanging above your sofa? What about in your bathroom?

The sofa is in the middle of the room, but Will Cotton’s portraits of our daughters flank our fireplace. Above the mantle, I have a Keith Haring. It was a lovely gift that he gave my mother after we collaborated on a photoshoot with Richard Avedon. It was done for the photoshoot and that was it. It’s inscribed to her.

In the bathroom I have four nude studies. A lot of the times when I’m in London or Paris, I will go into an antiques store and they will have a folder of sketches. You can kind of ferret out [great drawings]—although people are starting to charge more. I bought a folder of nudes and half of them were amazing so I hung them up.

Brooke Shields owns this painting by Kiki Carrillo. Photo courtesy of the artist.

What is the most impractical work of art you own?

My children! There’s nothing practical about having children, but they’re unbelievably beautiful. Nothing is impractical if it brings you joy. I don’t think I’m frivolous.

What work do you wish you had bought when you had the chance?

Every single time I’m at any event, there’s always something where you’re like “I should have gotten that”—and that’s the beauty of it. You’re dealing with something that’s one off, and that makes it sort of alive. You can’t have everything, and that’s probably part of the allure of it all. If I had unlimited funds, I probably would buy so much more.

Sara Issakharian, The Whispers. Photo courtesy of the New York Academy of Art.

If you could steal one work of art without getting caught, what would it be?

It would be a Stephen Hannock—the one in the Ritz, the huge huge huge one that covers the whole wall. I want to say it’s floor-to-ceiling, and it’s so beautiful.