All photos courtesy of Bonhams.
Cyndi Lauper has always felt different. Different from the people she grew up with, different from the glamazons in the pages of magazines, and certainly different from her pop star peers of the eighties. But instead of running from all those perceived discrepancies, Lauper embraced and even amplified her unique quirks, turning them into the very signatures that made her famous. She would tie a piece of tulle around her head to add height, draw on a winged liner to exaggerate her natural features, or dress in every color of the rainbow at once to transform herself into a freewheeling kaleidoscope on stage. For Lauper, these outfits weren’t just a means of expressing herself, but of making herself larger than life. More than just a musician, she is a walking piece of art, and fashion is simply her palette.
Now, the singer is putting a slew of her most iconic looks, possessions, and memorabilia up for auction with Bonhams starting today to give these iconic pieces a whole new lease on life. To mark the occasion, I met up with Lauper at the Bonhams headquarters to chat about her personal style, being a punk in an uptight world, and how there’s no problem too big that a little tulle can’t solve it.
THURSDAY 11:18 AM OCTOBER 15, 2026 NEW YORK CITY
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EMILY KIRKPATRICK: Hi, great to meet you. I’m Emily from Interview Magazine.
CYNDI LAUPER: Yes hi, I saw you downstairs.
KIRKPATRICK: I was really struck by your attention to detail with everything. Even when you came in and immediately corrected the disco ball.
LAUPER: It’s not perfectionism. When I was coming up, I knew what it should look like. I knew what it should sound like. I collaborated with people with like minds. I tried. When I didn’t know something, I asked. If I did know something and I disagreed, I would say, “I disagree, because…” If you have a vision, you just need to be crystal clear about what it is.
KIRKPATRICK: Absolutely. And I feel like that comes across in so many of these outfits. Were there ever times you doubted the clarity of your vision?
LAUPER: Absolutely. I was on Friday Night Live. I guess I wasn’t good enough to be on Saturday Night Live. I’ll tell you something though, I’m so grateful I did that show because first of all, Steve Martin came out and danced with me.
KIRKPATRICK: Amazing.
LAUPER: And not just him, but I met Pat Birch, who was the director of dance. I wanted to climb or do something. She looked at me and she said, “What if you rode that thing?,” which was the camera guy. He was on a jib. I was like, “I can?” I was so excited. But in that part of my career, she taught me so much and helped me do what I wanted to do. I wanted to do performance art. I wanted to fly. Who better could do that then? I was working with Mary Ellen [Strom], and these two avant-garde dancers. They were going to perform with me too, which I was like, “Oh my God, how great.” But in the end, I was very insecure about what I looked like. I felt like, “It needs to be big. What am I going to do?” I grabbed some tulle, tied it around myself and tied a bow, and I was like, “Yes, this is big and it’s color. And every time I move, color will go left to right on the screen—living art.”
KIRKPATRICK: Yeah.
LAUPER: Which is what I realized now as an older artist: All of that wasn’t just performance art. It was living art. I painted myself, I used color. I used sound, everything moved. So I’m so grateful that I did that show, even though it wasn’t Saturday Night Live.
KIRKPATRICK: I love how often tulle seems to be the answer to your problems.
LAUPER: Well, the problem I’m having with tulle nowadays is it’s just not made the same.
KIRKPATRICK: That makes sense.
LAUPER: It had a little more body to it.
KIRKPATRICK: I think the quality of so much of your clothing that’s downstairs, it does feel like we don’t make things that would even endure for this long anymore.
LAUPER: No. We do not make things like that anymore. The sewing is way different. And again, the fashion industry is being squeezed. It’s got to be made cheaper, cheaper, cheaper. And sometimes you put on a garment, and it’s made well or it’s an expensive garment not made well. You think you’re getting cheaped out, what about them [the people sewing the clothes]? What are they getting paid?
KIRKPATRICK: Absolutely.
LAUPER: And I feel badly too, because look at what’s happened to the creatives.
KIRKPATRICK: We’re churning through them.
LAUPER: They’re squeezed to make 12 shows a year, which is inhuman. And then what happens? So coffee doesn’t work anymore, you have a drink, give you a little sugar thing, then that’s not working.
KIRKPATRICK: Life speeds up to this impossible pace of production.
LAUPER: Impossible pace of production. Yes.
KIRKPATRICK: We’re both artists as well so we know creativity does not work on a schedule.
LAUPER: No.
KIRKPATRICK: Having 12 shows a season doesn’t mean you’re going to have 12 great ideas for 12 great collections.
LAUPER: Hello?!
KIRKPATRICK: It’s impossible.
LAUPER: And that’s just fashion, like, music too. Songs just happen. And if they don’t happen, you got to get off it for a little bit.
KIRKPATRICK: Right. Also, I loved what you said earlier about the self-expression of the ‘80s and us losing that today.
LAUPER: Well, the individuality. If you don’t hold on to that, what are you doing? I’ve never relished or set my cap on becoming a sheep. You know? Whether you’re a terminal sheep or you’re going to be there forever. I had off this summer, so I went to museums. I went to Spain, and I went to the Balenciaga Museum. I saw different fashion things like, in Brooklyn, there’s a fabulous designer that—
KIRKPATRICK: Oh, Iris Van Herpen?
LAUPER: Yeah.
KIRKPATRICK: At the Brooklyn Museum, I interviewed her for that. She’s incredible.
LAUPER: Yeah. And she worked for McQueen too.
KIRKPATRICK: What she does with technology and the fabrication, I don’t know anyone who’s pushing the limits of material like that.
LAUPER: Oh no, there’s young ones doing stuff. They just need to be nurtured. And that’s what this is about, to inspire people. That’s it. Remember individuality, that’s where the creativity comes from. You’re not going to think like somebody else. You’re not going to be like somebody else. My big lesson in the ’80s, I looked at all the people who were on the charts with me and I wasn’t like them. And I thought that was my demise. Why do I have to be so different? But it wasn’t. It was my endurance. That’s what made me remember, “You are an artist and you’re going to be walking a path sometimes where there’s nobody ahead of you. Too bad. Keep going. You’ll find it.”
KIRKPATRICK: Yeah. And the people will find you too. You resonate with it.
LAUPER: Icons resonate together.
KIRKPATRICK: Absolutely. That was something I was thinking about while you were explaining the makeup choices you made, or the tying of tulle around your head to make your hair bigger. It’s like you were correcting these perceived flaws or differences that you had, but actually it’s making them stand out more, and that’s what made them iconic choices in the end.
LAUPER: Yeah, yeah.
KIRKPATRICK: It’s the way that we try to conceal ourselves. Ultimately, those unique things are what make people.
LAUPER: Well, I needed to be bigger. And I wanted color because, with color, as you twirl across the stage and you look at a stage, you see color. And I was always moving. So if you had layers of color, that makes a big difference. Because you’re painting too. You’re living art.
KIRKPATRICK: Right. And you’re creating an overall effect and image for the audience.
LAUPER: You’re creating art and music. And that’s what I always wanted to do.
KIRKPATRICK: Yeah. It seems very holistic, your vision of what you were creating.
LAUPER: I always want to try it and see, “Can we move it over here?” If it don’t work and it sucks, we can always move it back.
KIRKPATRICK: That goes back to your earlier point about just asking questions. Take the feedback and evolve from it, which I feel like sometimes artists can get very stuck in their idea or perception of themselves.
LAUPER: Yeah. You can’t read your own press. We always had a joke, like, “Go ahead, tell them who you think you are.” But it’s almost like, “Yeah, they don’t understand the song. Tell them what you thought it was saying.” But listen, it’s a journey.
KIRKPATRICK: Yeah.
LAUPER: I wanted to share at this moment. I thought it was important to open it up and put it out there. And plus, I’m not wearing it. You can’t wear the same things that you wore back then.
KIRKPATRICK: Sure. You evolve.
LAUPER: I just don’t want to be conservative, that’s all. I’m not going that route. I always embrace Bohemian culture because that’s where all the artists live.
KIRKPATRICK: Yeah, definitely. I’ve noticed too with myself, as I’ve gotten older I’ve made a more concerted effort to make sure people know that I’m not normie. Sometimes I think I dress very preppy and so I have crazier glasses as a way to communicate to other people, “This is a safe space.”
LAUPER: You could go preppy punk.
KIRKPATRICK: I was a preppy punk in high school. I had a dress code, but I didn’t want to look like everyone, so I was punk. In rural New Hampshire, which was interesting.
LAUPER: Oh, New Hampshire. I always thought with New England, it’s nice to hear everybody talking like the Pepperidge Farm commercial. But after a while, I just wasn’t blending. There are artists there. When I lived in Vermont, there was a whole bluegrass thing going on that was incredible. But I wasn’t that either.
KIRKPATRICK: Exactly.
LAUPER: And I didn’t stay long enough because one, I’m allergic to the cold. Two, I wanted to see the ocean. I can’t live without that. I grew up with the ocean right here.
KIRKPATRICK: I also grew up with the ocean. I’m thankful my mom is an artist and I had her as an outlet because I agree, I felt like, “These are not my people.”
LAUPER: This is not my tribe.
KIRKPATRICK: Yeah. “I got dropped in the wrong location.” But having my mom and just seeing her express herself and be different, that alone opens your mind as a young kid. And same with looking at your clothes. I think it opens people’s minds like, “Oh, this is possible.” Also that there are designer pieces down there, but it’s not all designer stuff.
LAUPER: Yeah, it’s like you’re wearing a Dolce chub [coat], and you think that it’d be nice to have a derby that’s not only the same color, but with feathers. It’s within your wheelhouse because they still sell glue.
KIRKPATRICK: Michaels is still open. There’s less and less of them, but they’re still there.
LAUPER: Oh, that’s right. There’s one Michaels. There was Lee’s art. There were art shops. There’s no painting shops anymore.
KIRKPATRICK: I know. We’ve lost all of them. Curating this collection, was there anything that you were surprised either that you held onto or that you ever wore?
LAUPER: Well, there was a few pieces I didn’t know left. I was like, “Uh-uh.”
KIRKPATRICK: “Where’d that go?”
LAUPER: Yeah. But no, not with the clothes because I was in with the clothes.
KIRKPATRICK: Yeah. It seems like you have an encyclopedic memory of most of what’s in here.
LAUPER: Because I know the color hair I had. I remember the photo shoot. I was involved in it. We were creating it together. [Flips through the catalog of her clothes and points to an outfit.] This was always my favorite thing. We had suspenders, but they weren’t regular suspenders. They were the short ones. Because when you wore the corsets, you needed suspenders to keep it up. Otherwise, your tits are out all the time. And so that was a fabulous moment. And oh, look, see how polka dots go good with floral?
KIRKPATRICK: I know. Your eye for pattern matching, I don’t know that I have the same.
LAUPER: I did a show once, and I don’t know if she has it in here. All the long johns were rolled up. I never wore it flat, but see, look how fabulous.
KIRKPATRICK: Yeah, amazing.
LAUPER: And a young kid could still wear that today.
KIRKPATRICK: Absolutely.
LAUPER: With a big beach hat.
KIRKPATRICK: Totally. I see it. [Lauper turns the page.] There’s the beach hat.
LAUPER: That’s the ‘80s beach hat though. I can’t find it, but I had a shirt that was made out of a kirchief pattern. And I had these blue checked pants, and I wore them together. And I sang, and the person reviewing it was so upset about what I was wearing that that’s what she wrote about.
KIRKPATRICK: “Couldn’t even hear the music.”
LAUPER: “Her clothes were so loud, I couldn’t hear her sing.” And another woman said that once. I went downtown to Jimmy [Webb] at Trash and Vaudeville when it existed.
KIRKPATRICK: Yeah.
LAUPER: Jimmy was fabulous. I said, “I’m going to sing for Boston Pops and blah, blah, blah.” And my hair was white and black. He had this silver outfit, it was short and I wore fish nets. So what does this woman say? She said, “Well, her clothes were so loud, I couldn’t hear her sing.” And I’m like, “Who are these people? It’s rock and roll.”
KIRKPATRICK: Yeah, and it’s just an outfit. You really can’t see past it?
LAUPER: Rock and roll, not Mother Cabrini.
KIRKPATRICK: How are you supposed to show up? What would be appropriate?
LAUPER: They were very corporate. And so if you wanted to do a certain magazine and you were rock, like a real one, and not pretending that you are high fashion, you didn’t get in those magazines.
KIRKPATRICK: Right.
LAUPER: And that was her excuse.
KIRKPATRICK: “The outfit’s too loud.”
LAUPER: Honestly, it’s okay by me. Because here I am still working.
KIRKPATRICK: Absolutely.
LAUPER: What did Dolly Parton say? “It’s very expensive to look this cheap.”
KIRKPATRICK: Exactly. Live by it.
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