Molly Ringwald: You’ve always been such an icon for me in terms of how I want to look. You’re very fashionable but you never look like you’re a slave to it. You just have this flair. What is your first clothing memory?

Cindy Sherman: Oh gosh, I was maybe eleven or so. And because I loved paper dolls, I made paper-doll versions of all the clothes I would wear to school. I had a little pegboard with days of the week, and on the weekend—Sunday night, I guess—I’d figure out my outfits for the whole week ahead.

MR: That’s so sweet. You probably don’t have them anymore.

CS: No. But when I was in college, I remember thinking about it, and I did an art-project version of the same thing, only without the days of the week. I just made a doll of myself with my underwear, and photographed all my clothes, and made it into a little children’s book of school clothes, play clothes ... Then I made an animation from it. It’s sort of how a lot of my work evolved, out of that.

MR: When you first started making art and taking photographs, did you know that it was going to be only you in the pictures? Did you ever think you were going to include other people?

CS: I don’t remember thinking about it one way or another, but I didn’t expect to be doing basically the same thing for thirty years. I guess in the beginning I thought, I’m doing one project that is using myself, and who knows what I’ll do after that? I did try shooting other people at times—friends or family members. I even paid somebody to model, but it made me so self-conscious. I just wanted to entertain the person.

MR: When you’re thinking of a new character, do clothes always play a part?

CS: A lot of times the clothes actually determine it. When I did the clowns, I was researching them online. I didn’t want to just buy clown outfits, which you can easily get. The imagery online that I was interested in, or influenced by, was of clowns who looked like do-it-yourself clowns. People who just looked funkier appealed to me because I started to wonder, (laughs) Is that an alcoholic hiding behind this clown mask? What’s under the clown makeup and the funky costume? So I would go online, like on eBay, and look up, I don’t know, colorful clothes, and I found square-dancing dresses with these crazy ruffles and everything. Or I’d go to the Salvation Army and get a bunch of brightly colored striped T-shirts. I would amass all this stuff and then play with it, mixing things up, and then from that I would figure out what the clown should look like, and have more of an idea of the personality of that clown.

MR: When you do a portrait, do you feel you know the character—in terms of biography? Or is it more the essence of somebody?

CS: It’s more like an essence. With some of the society portraits, as I’m shooting them, as the character is evolving, I will start to feel I know the character, or maybe I’ll realize the shots that work the best are the ones where she looks very haughty and bitchy and distant and cold, and that will help inform the character even if I didn’t plan on making her that way. Some of them look more haunted and sad and are trying to put up a good front. But it’s always a surprise to me when I see the results in the tests. Then I realize, “That’s the one that works.”

MR: I think I’ve told you this before—but when we were working together on the movie Office Killer, I remember thinking about my character’s clothing, and I had this idea that she was going to be very New York and wearing all black, you know, because she was written kind of bitchy. And when you came in you were like, “No no no.” You were very forthright: “Wrong, wrong, this is not right, she’s colorful, she has to have really bright colors.” I hadn’t thought of it that way, but as soon as you said that, and we started to build the character around these colors, it really changed the way I saw the character, and she ended up being a lot more funny and interesting. She was still really bitchy, but the color really informed my interpretation of her. It’s something I’ve thought about a lot since then.

CS: I like to make characters who are not supposed to be frumpy—to dress them up frumpy and take it in an opposite direction.

MR: Do you ever find yourself wanting to photograph people you see on the street, like, Oh I have to remember that outfit?

Women in Clothes cover

CS: Sure, yeah. And I’ve tried to do it surreptitiously. Usually the person’s approaching me and I’m trying to find my phone really quickly and then I pretend I’m just looking at my phone, and usually the picture is way out of focus or I catch the person from the side or the back. Recently I was in Venice and a bunch of us were having lunch and there was this waitress who was incredible—I have never seen anybody with so much mascara on. It was as if she used a whole thing of mascara in one sitting. It was caked on in the most outrageous way! I wish I were one of those people who don’t mind going up to a stranger and saying, “Wow, can I take your picture, you look great!” That would make sense if they’re really attractive, but if they’re very strange-looking ... maybe they don’t know that they’re strange-looking. It might be a little insulting or something. So I make mental notes.

MR: Do you feel women in general take enough risks with what they wear? 

CS: Well, I don’t think celebrities take enough risks—especially celebrities who have a creative side and probably know exactly what they feel good in. But that’s because they get torn apart in the press so much they’re afraid of taking chances. So everybody just looks very tasteful and kind of all the same.

MR: Yeah, bland.

CS: Yeah. So for somebody who likes to watch celebrity events, it’s sad to see everybody look the same. But the general public? I think most people see themselves one way, and that’s how they always see themselves, even as they get older, like wearing the same hairstyle forever. They hit a certain look when they’re twenty-five and continue to look that way until they’re old. Men and women.

MR: Most fashion people actually counsel you to do that—to keep one hairstyle, like Anna Wintour or Jacqueline Kennedy Onassis. They really picked a look and didn’t deviate very much.

CS: That’s true.

MR: I feel I took way more risks as a young person. I’ll look at old photographs of myself—or even old movies, because that had a lot to do with my clothes—and I’ll think, “Wow, I was really bold, I was really going for it there.” I never really thought in terms of what other people were going to think. Now I’m not a neutral dresser, though I certainly don’t take the risks I used to take. Do you find you’ve gotten riskier as you’ve gotten older? 

CS: I think so, because when I was younger, especially when I was starting to get more successful, I felt so guilty about it that I didn’t want to stand out. I’d go to an opening and just try to blend in. Now it is what it is. And I can afford to experiment more with shopping and purchases, so I definitely feel more playful.

MR: I feel like you’re a lot sexier. 

CS: Ha! That’s nice.

MR: I always thought you were great looking, but you were more ... I don’t know ...

CS: I was tomboyish, I think.

MR: And cute! I wonder if that had anything to do with ... Well, you were at the tail end of not such a happy marriage. Do you feel your clothing is influenced by the person in your life?

CS: Yes. Although I think what also happened is I became single again and I was starting to get older, and I wanted to recapture some femininity I felt I lost through the unhappiness of the marriage or my youth going away. I also was so much more insecure about my body then, and I felt so much better about myself after the divorce that I didn’t mind letting more of my femininity come out.

MR: It was really interesting to see that transformation. It’s also great for me to know somebody who looks better as she gets older (laughs) rather than the other way around. Because I think aging is really, really rough.

CS: It’s scary, yeah.

MR: It is! It’s fucking scary! There’s part of me that wants to say, “I’m deeper than that, this shouldn’t matter, think about the roots of the tree rather than the flower.” And I do. There’s a part of me that really believes that. Then there’s the other part of me that’s just like, “Fuck, it’s only going to get worse.” 

CS: I know, it’s really scary.

MR: But in a lot of ways, I’m better-looking now than I was in my thirties. I’m more confident, my body is better because I think about it and work on it.

CS: I totally agree.

MR: How do you feel about the way culture sees and presents women to women?

CS: I think it’s scary what the fashion world presents as women. But I also know that when I’ve had my picture taken and they’ve done a tiny bit of retouching, I actually am thankful. They show me the before and it’s like, “Oh god.” But it’s these models, I think. It’s not so much the retouching, it’s the choice of models. They could still find really beautiful people who weren’t necessarily so skinny, or they could find really interesting faces that weren’t classically beautiful.

MR: They don’t look quite human to me. I feel like I’m conditioned like everybody else to think, “Oh, that’s pretty, that’s beautiful, they’re so elongated,” but when I really think about it, they’re just not like anybody else.

CS: Yeah, they’re freaks of nature compared with the rest of us.

MR: And freaks of nature that go in one direction rather than another. Fashion’s always been around, but there’s a lot more pressure on girls to look a certain way. I love your centerfold pictures, because most centerfolds are so fake and the women don’t look real.

CS: I made them for a magazine as a response to the idea of a centerfold. But I wanted it to feel like you were intruding on somebody’s intimacy, rather than feeling like you wanted to gawk. I wanted it to make you feel like, “Oops, I better turn the page.”

Adapted from WOMEN IN CLOTHES by Sheila Heti, Heidi Julavits, and Leanne Shapton with permission of Blue Rider Press, a division of Penguin Random House.  Copyright © 2014 by Sheila Heti, Heidi Julavits and Leanne Shapton.