Costumer Mona May created many of the iconic, nostalgic looks this generation is obsessed with, dressing the characters of sartorially-elevated comedies like Clueless, Romy and Michelle's High School School Reunion, Never Been Kissed, Night at the Roxbury, and The Wedding Singer. May dressed visual artist, rising musician and underground queer shapeshifter Dorian Electra in some of these instantly recognizable looks before the two joined in conversation for a candid chat about high-low fashion, gender identity, labels and why the actor should always wear the costume, not the other way around.

Dorian Electra: How did you get started doing costume design?

Mona May: I had always wanted to be a fashion designer. From the time I was a little kid I was drawing pictures of clothes and dressing everybody including my mom and organizing friends' closets. That was my passion. Later, I was studying in Europe, then I was in New York and when I got to LA, I had a bunch of friends in film school at USC and they asked me "Hey, you do fashion, can you help us on our thesis films? and I was like, "Sure!" And that's kinda how it all started. Really by chance I got this opportunity to get involved in filmmaking and I really loved it from the beginning, loved the process and I loved creating characters from the pages of a script and bringing them to life.

DE: What were some of the most fun characters for you to create looks for?

MM: Clueless I think will always be one of my most fun ones because it was such a nice beginning of my career and it really married something that I love so much, which is fashion and costume design. Everything at the time of prepping the film was grunge and Kurt Cobain and girls really didn't look really "girly" at the time, so I had to look at the European runways for inspiration and predict what would be cool and then mixing high fashion and low fashion, designer and thrift store, which also wasn't really done at the time. All that runway fashion had to be translated into each character so it felt real.

"Clueless"

DE: I think people of my generation are so used to seeing the mixing of high and low fashion that we take it for granted. Most iconic example of today is probably Cardi B, like Gucci plus Fashion Nova. And it's crazy now the speed at which we see trends move from the runway to cheap knock offs on Amazon. Like the big square rhinestone Gucci sunglasses or the hype beast revival of the Kurt Cobain mod glasses, that someone who wants to be "on top" of trends can now do so in a relatively timely with fashion without having to buy the originals. What are your thoughts on that?

MM: Well, you know it was very different than when we were doing Clueless 20 years ago. We didn't have computers, we didn't have Style.com, so it was a very, very different kind of process. I think that what's so cool about at the time not having so much information is that you could actually create something fresh that people hadn't seen before. It was more original. And then movies had a lot more impact, especially on fashion, because information wasn't coming from everywhere at you. And I think right now with the overload of information, the problem is that people get very confused and I think some people don't really know how to dress anymore. Like they put as much trendy stuff on themselves as possible without really understanding their body or who they really are.

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DE: What do you think "true style" looks like?

MM: To me, true style is really when you take the information that's out there, but then you translate it into your own world, who you are, how old you are, where you live, what's the complexity of your character and who you are and your actual body/shape. It's should feel soulful.

DE: Your looks are so iconic that they've been ripped off or paid homage to so many times in photo shoots, music videos, movies, Halloween costumes. In fact, even for this shoot we ended up ordering the 'official Clueless Cher Halloween Costume' from HalloweenCostumes.com, which I thought was really nuts and hilarious, haha. How did you feel about that?

MM: Fantastic. I mean, I think it's fantastic. It's a form of flattery. Like when Iggy Azalea and Charli XCX did their spoof [the "Fancy" music video]. It's great that people continue to feel that these looks are important and they want to express themselves with these characters, I think is phenomenal. I hope that it continues for another 20 years.

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"Night at the Roxbury"

DE: What was the hardest challenge to overcome in creating these looks?

MM: Comedy is very difficult to design costumes for because it's very easy to overdo it. You have comedic actors like Adam Sandler or Will Ferrell or Lisa Kudrow who are very funny already, so the costume really has to be flow with the character, and can't overwhelm them in anyway. The actor should be wearing the costume, the costume shouldn't be wearing them.

DE: What excited you the most about the concept for this photoshoot?

MM: From the beginning when I met you, I saw you were wearing this amazing checkerboard suit and you were very intriguing to me and when I found out that you were gender fluid, that really piqued my curiosity. And I immediately felt like it would be something fun to do. I mean you kind of transformed these characters into something completely different and fresh. When we were doing the fittings, it was really interesting with the Clueless look, since we wanted to make it more boyish and turn the skirt into school boy shorts, how you immediately took that on with your stance. But how did you feel in it? The process was so interesting to me.

DE: It was really cool how you had suggested getting an oversized costume, so that immediately when I put it on it felt comfortable and boyish and gave me this like boy band vibe or something that was super easy to play with!

MM: Definitely, and I think with the Romy and Michele look, what I loved a lot was both the boyish and the ultra feminine and the juxtaposition of these two characters together. And again, it's so cool that it's one person doing it. I mean, you were so cute as Michele, adorable, gorgeous, feminine, beautiful. The hair, the makeup, the nails, the pink heels. And then the juxtaposition of Romy, where we tried to masculinize the original blue dress by making it into more of a tunic, with the turtleneck and the baggy pants and the silver hiking boots, with the kind of sixties glasses and the hat helped to make it something original.

"Romy and Michelle's High School Reunion" and "Zenon: The Zequel"

DE: That was a super fun one. I definitely felt like I was in full drag when I was dressed as Michele.

MM: Just wondering, why would it have to be called drag? Because drag is like a costume?

DE: Not that drag is necessarily a costume, because I think it can be many things for different people. But for me personally, I tend to feel like I'm "in full drag" if I'm wearing something that's an extreme departure from my normal looks, whether it's extreme over-the-top feminine, like Michele, or extreme over-the-top masculine, like when I dress up as Bono and contour on fake abs. But then I'll do characters (like A Night at the Roxbury or my used car salesman character, Don Bogman) that I don't necessarily feel like are drag either! So as you can see, the line isn't always clear.

I just know that when I wear my usual three piece suit and draw on a thin mustache, I don't feel like I'm in drag, I just feel like myself. But maybe that's confusing! I definitely have had way more feminine periods of my life in the past and sometimes it fluctuates for me based on my mood or what the event or day calls for you, know? When I was a kid, I wasn't into really feminine stuff but I also wasn't really a tomboy because I wasn't sporty at all and I didn't like the outdoors. I just watched a lot of TV, and I mostly felt pretty gender neutral as a child. But I was really lucky because my parents were very chill and didn't put any pressure on me to be any certain way.

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"Never Been Kissed"

MM: Oh yeah, when I was a kid I hated dresses, I hated pink. I was totally into sports and played soccer and you know, at the time when I grew up in the sixties, there wasn't really girls' stuff that wasn't pink or purple. I was always like, "I don't want to wear that!" I find it kind of interesting that now we have so many labels because I think it's so natural to human beings to be kind of floating in a sense, you know. I think being more open is just as important and not being always so labeled.

DE: Yeah totally. I know what you mean about labels. I think a lot of people find labels to be very liberating though because it allows them to have a name for how they identify, and allows people to be able to understand where they're coming from. I mean, I even resisted the label "gender fluid" for a while because I was kinda just like, "Well, I'm just me," you know? But I think that's because I was really lucky to have grown up in an open and supportive environment where I could be free to be myself without having to explain it to anyone, so I never felt like I needed a label. But so many people never had that support and still don't have that privilege.

So many people still have to defend and justify who they are every day even just walking down the sidewalk, and have to defend themselves against, not just emotional, but physical violence because of who they are, especially trans women of color who are statistically the most targeted. And ideally, yeah, it would be awesome to not have to have any labels. But I think in a world that is still so obsessed with the gender binary and the idea of sex and gender being inextricably bound, I think it's important and empowering for someone to be able to say "I'm non-binary," "I'm trans," you know? And use a label to actively defy those norms.

"The Wedding Singer"

MM: Absolutely. Hopefully the new kids who are being born now, by the time they grow up, there will be a lot more acceptance in terms of acceptance of masculine, feminine and any way in between, and hopefully the labels won't be as necessary. I think that what you're doing is awesome and I think what's fun about this photo shoot again, it's kind of like empowering with creativity, empowering with transformation, empowering who you are, and you know, because these characters are so beloved that we can have fun with it, you know? So the gender fluidity, the is it drag or is it not drag, the masculine, the feminine, is all part of the playfulness of everything that we've done. Working with Sequoia [the photographer], Ally [the makeup artist and hair stylist], and Weston [who assisted on the shoot and who helped direct the character impressions] was so wonderful, how everybody contributed to it, it was like in a really good spirit and that's what shows in the pictures, that we had a lot of fun.

DE: I know I had a blast!

MM: It was just a really great experience to collaborate with you. And it's like how do you inspire the young people who are maybe fluid or transgender or whoever they are, that they can feel it's okay to play and be themselves and I think that's what creativity really is, it's being playful, being open and doing the unexpected.

Model/Producer: Dorian Electra
Photography: Sequoia Emmanuelle
Styling: Mona May
Hair and Makeup: Ally McGillicuddy
Assistant Photo Editor: Weston Allen
Special Thanks to Emma Tolkin and Liam Moore

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