Hey, Regina: An Interview with Founder Regina DeSantis
by Tiffany Chu '22
The first issue of Hey, Madeline was distributed on October 5, 2009.
A decade and several rebrandings later, Hey Madeline has become W.Collective. In honor of ten years of fashion and lifestyle at Wellesley College, in late 2019, I spoke with Regina DeSantis, the founder of Hey, Madeline, about how it all began.
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TC: I was reading your Letter from the Editor from the first issue of Hey, Madeline...
RD: Oh god [laughs]. I look back on a few of the things I wrote and think, “Oh geez!” You live and learn.
TC: You mentioned that it started as a sort of dress-making operation: Dresses by Regina? Can you speak a bit about that?
RD: I was in high school…a million years ago [laughs]. I actually went to an all-girls school from pre-kindergarten through my senior year of high school, then spent four years at a women’s college. During high school, I would doodle dresses, and a couple of my friends noticed. It became a thing—I would draw dresses for friends. We would all carry binders to class, and sometimes people would put my drawings in the front of their binders. Actually, I had a few friends who ended up getting their dresses made for senior prom, which was really cool!
TC: How did you get the dresses made?
RD: Where I grew up, there is a big “Sweet 16” and wedding culture, and we have dressmakers who make elaborate gowns for events. A couple of girls took what I drew, modify a little bit—I would draw very high-fashion designs, but maybe they weren’t the most prom-appropriate attire—and get [the dresses] made. In fact, I designed four different dresses for a friend’s little sister’s Sweet 16—three “dais” members’ gowns and the birthday girl’s dress!
TC: That’s amazing! How did you make the transition from Dresses by Regina as a sort of dress-making enterprise to Hey, Madeline the magazine?
RD: I’m so flattered you called it an enterprise! When I was at Wellesley, there was a fashion group called a La Mode, and they had a student fashion show every year. For my nineteenth birthday, my parents gave me a sewing machine. I had I decorated my dorm with a few of my dress sketches, and the idea came to me to create a few pieces for this fashion show. I had a couple of friends model the finished clothes.
I’ve always loved writing. I was an English major in college, and my current job involves a lot of writing. The original saying for Hey, Madeline was, “Fashion is what makes you tick.” I’d always thought of fashion as art, so I asked myself, “What is a good way for me to blend those two things (art and writing) together? Start a fashion newsletter, since we don’t have that at Wellesley!” The idea came to me during the summer before my second year. I contemplated starting it online, but I did not think we’d get a solid reader base that way. Smartphones weren’t nearly as ubiquitous as they are now—I didn’t have an iPhone until my senior year. One day, I finally said to myself, “Okay if I don’t do this now, at the beginning of the semester, I’m never going to.” So, I took a few pictures of willing friends who wore interesting outfits and wrote a “Letter from the Editor.” I think the very first Hey, Madeleine was nothing but pictures and a couple of captions!
Full disclosure, it was a Word document—we were using Microsoft Word for a very long time. We printed them out, distributed them, and then waited. I thought, “Well, either this is going to be super embarrassing…or somebody’s going to read it.” I guess both happened because we improved over time. Again, sometimes I look back on our first few issues and wonder what I was thinking, but we don’t learn unless others share their ideas. That’s how a school committee, this student group, began. Naturally, I’d had the brilliant idea to start a student org at a time when Wellesley had a freeze on student organizations because of the Recession! My amazing mother funded the first several publications. She was great and so supportive. I didn’t study abroad junior year because I knew I had to stay on campus to make the case for Hey, Madeline and be present for it. I’m so glad we were able to secure funding. Once we had funding, we said, “Ok…let’s get this glossy and bound!”
Regina in December 2019 featuring her Wellesley diploma and her Wellesley best friend's hoop on the wall (left). Regina in October 2009, from the first issue of "Hey, Madeline" (right).
Regina during her senior year in a shirt featuring the original Hey, Madeline carousel logo (left). The inside of Regina's Wellesley class ring, reads: Hey Madeline (center). Regina and her mother, Hey Madeline's original publisher (right).
TC: What do you think is the value of writing about fashion and lifestyle amidst everything else that’s going on in the world?
RD: This is something I thought about when it was brought to my attention that the magazine formerly known as Hey, Madeline had a name change [to W.Collective]. I think it was a necessary facelift, if you will. We wrote about fashion, we wrote about lifestyle…the things we prioritized and valued in 2009 through when I graduated in 2012 were great, but might not be relevant in a 2019 world. Nobody wants to read about Tory Burch Reva flats! We want to talk about sustainable, inclusive fashion. We want to talk about designers creating outfits for actual human beings of different sizes and shapes, and we want to see models who reflect what the United States—and the world—actually looks like. I love Kate Moss, but not everybody looks like her. I think when it comes to writing about fashion and lifestyle, there’s always sort of an eye towards idealism—high fashion is artwork, and it creates a story. You can create the image, but I think you should ask yourself how the fairytale translates into what real people wear. I would love to walk around in a ball gown every day, but that’s not realistic.
TC: I also saw in your first Letter from the Editor that you were hoping to expand the magazine to encompass other forms of art in the future. What was your dream vision for the future of Hey, Madeline?
RD: You probably noticed the last few issues we did had hand-drawn covers—friends of mine drew them. The last issue I was part of had a cover image modeled on Grace Jones. [These cover pages] were a form of art. We also covered the Davis Museum when they sponsored a student art showcase. The Davis had a visiting artist, El Anatsui, do an installation at the museum. He uses recycled materials to make sculptures resembling kente cloth. The Davis invited students to create wearable art using non-traditional materials. One student, who was part of Hey, Madeline, made a beautiful wedding dress using coffee filters and cigarette butts.
Also, I wanted as many student voices as possible. I didn’t want the magazine to only reflect what I liked and what I thought was interesting. My dream was that any Wellesley student could open the magazine and identify with some piece of it. Maybe someone would think, “this article’s great,” or, “look at this photoshoot...my friend is in that!” This was always very important to me. A later issue, published after I graduated, featured an article discussing buying a chest binder. I thought that was great.
I think back to some of our old photoshoots also. Photoshoots are really difficult—they involve a lot of prep-work and moving parts. It was definitely fun, but there was so much work in getting the space, setting up for the space. At any given minute, I’d go through a running checklist in my head—who is in makeup? Who’s in hair? Who’s in front of the camera? Did the model show up? Are we sticking to the concept? It was worth it, though.
One of my favorites was the makeup-driven photoshoot from my second-to-last issue. I called it “the blue issue” because the color blue was featured prominently.
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Regina in 2009 (left). Letter from the Editor photo, 2011, collaborative photo shoot with a boutique in the Ville (center). Regina near Punch's Alley at her 5-year Wellesley reunion in 2017 (right).
TC: Was the photoshoot called Living Canvas?
RD: Yes! It was based on a photoshoot with a model named Anja Rubik, called “Peintures de Guerre,” which roughly translates to warpaint or warpainting. I thought the makeup was so cool and wanted to try it—our makeup director had also acquired a professional kit at that point, too. The morning of that photoshoot, I remember calling a friend of mine and saying, “Hey, we're short on models so I need you to get to the Jewett Art Center. Don’t put on any makeup—we’ll take care of it. Just get here now!” That was probably one of the best photoshoots we’ve done. Our photographers have been wonderful.
TC: How did you first assemble the team for Hey, Madeline?
RD: When we first began, I’d basically set up an open invite to anyone interested. A few people reached out to me directly, through a friend of a friend, or by email. Over time, after getting input from others, we separated into three teams. We would specifically advertise our org based on these teams—students could apply to the photography team, the writing team, or the layout team. Our goal was to give people their niche, because wearing multiple hats makes it hard to prioritize and you risk having to cut corners sometimes. You want people to focus on what they want to be doing.
Having an online presence is always a good thing. There are resources now that didn’t exist ten years ago—you have social media channels and more people are “plugged in.” There’s Instagram, there’s Facebook. I’ve noticed that W.Collective has a really great online presence, which I think is important.
TC: I actually wanted to ask another question about that. What do you think about the transition from distributing print magazines to publishing content mainly through the website? While most publications in the “real world” are starting to be more successful when they embrace digitalization, do you think the physical nature of print magazines reaches a wider audience at Wellesley and on college campuses in general?
RD: It’s interesting because ten or so years ago, I remember a few Hey Madeline team members were talking about expanding online—I was stubborn and refused. Now, I think it is necessary to go digital. I think the written, printed word is never going to go away completely, but in today’s world, with rapid consumption and limited time, things need to be available in iPhone format or online—not just in print. Also, printing is expensive, which again is unfortunate, because I’m an English major and will always have an affinity for holding a book or magazine. But, realistically speaking, it’s important to have an online presence. When I think about over the years how many print publications have either gone out of circulation or are only available online now, the writing is on the wall…sorry for the pun. I think W.Collective becoming primarily digital was a wise decision.
Outtake from a 2010 photo shoot (left). Regina in a black gown for a friend's wedding, Winter 2017 (center). Regina in Winter 2018 wearing a quintessential outfit featuring a black dress, a 1961 purple Hermes scarf, her mother's watch, Wellesley ring, and pearl earrings received as a bridesmaid gift in 2016 (right).
TC: How do you think your involvement with Hey, Madeline shaped your career path and interests?
RD: In a lot of ways, Hey, Madeline was basically my college major. It was—sorry, mom and dad!—it was my priority, it was my baby. Hey, Madeline defined my time at Wellesley. I gave everything I had to it, so I am beyond thrilled that it still exists and it evolved for 2019!
I said before—my job involves a lot of writing, and I’m also an evening law student, so that too means I spend a lot of time writing. My background is health policy, which is probably the farthest thing from fashion, but being able to write—and being able to write in different ways—has helped my career. The way you write for editorial is different from the way you write a memo, and that’s different from a policy analysis, and that’s different from a legal brief, and that’s different from a professional email. So, being able to write—and being able to gauge what kind of writing a situation requires—has been invaluable. I can’t write an English essay for everything, as much as I’d like to...
Also, this might be unrelated—part of me wonders if anybody knows where the name Hey, Madeline comes from?
TC: Where does the name come from?
RD: It’s because...well, you know teenagers do this: I was nineteen and listening to a lot of emo things [laughs]. It’s a Jack’s Mannequin reference! It goes back into what went into creating Hey, Madeline. There was a lot happening in my life at that point, and I was listening to a lot of Jack’s Mannequin. I heard the line and thought, “oh, this is a great name.”
TC: You mentioned earlier that you went to a girls’ school and then you went to Wellesley. How do you think being in these historically female-oriented environments encourages students to dress in certain ways?
RD: I was in a uniform for fourteen years, so I actually didn’t know what to wear to class my first year of college. When it comes to an environment influencing individual fashion, I think it depends on who the person is, how the person wants to dress, opinions on clothes in general, and what that person wants the world to see. In some ways, [this environment] might make a person more fashion-conscious, and in some ways it might make a person less fashion-conscious. That’s not just for shallow, stereotypical reasons—a person might think, “I feel safe here, so I’d like to dress this way.” Or, “I just got this really cool, funky pair of shoes—and I know my friends will notice!” Maybe people will not want to get dolled up at 9 am for class and that’s fine, too! I think maybe being in a female-centric environment is a safe space and a free space.
TC: This is kind of a cheesy final question, but when you wake up in the morning who do you dress for?
RD: Oh wow…what did I write back then?
TC: “For your friends, your boy, your girl, your hot professor…”
RD: I cannot believe I got away with writing that! Again, some of my old Letters from the Editor…sorry, mom and dad!
I work in an office setting, so I can’t exactly wear ripped jeans. It’s funny…over the years, my closet has gone kind of in one direction—I basically wear black all the time. It’s always appropriate. You can dress it up, you can dress it down, and it hides how frequently I drop coffee on myself! It’s actually a running joke among some friends of mine: “Which black dress is Regina wearing today? Is it the one with short sleeves or long sleeves?”
…I dress for myself, of course!