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Discover Top 10 Iconic Magazine Covers That Defined A Teen Vogue Editor’s Career

When I was a teenager, there were magazines everywhere – in the doctor’s office, in the magazine aisle of the grocery store where my mother shopped, stacked on the babysitter’s couch. The really good issues were passed around by parents in my neighborhood. The pictures on the covers impressed me, but only in the sense that I wanted to understand what was going on in the minds of teenagers and celebrities. How was the sausage made in the magazine? That was to remain a mystery to me for decades.

Around the same time, Phillip Picardi was also thinking about magazines in Boston. He went on to have a magazine career that kids could only dream of – working at Teen Vogue during its most political times, founding the LGBTQ magazine Them, serving as editor-in-chief of Out magazine, and working for Refinery29 and Allure. Now Picardi has returned to his journalistic roots and is working on his own: he’s a master’s student at Harvard Divinity School and runs a popular newsletter, Religiously Blonde, and a podcast, Unholier Than Thou, that explores the intersection of religion, spirituality and culture. We spoke with him about 10 images that have inspired his career (and the tarot).

1. Saint Sebastian

Saint Sebastian by Guido Reni, 1615–1616

“Of all the saints, Sebastian seems to have fired the gay imagination the most. Almost all art historical depictions show him as a lithe young fellow tied to a tree and – ahem – being pierced by a whole series of arrows. It took me a few years into young adulthood to realize why I was so drawn to these images. (Don’t worry, it has nothing to do with the blood.) Oddly enough, while St. Sebastian was a martyr, as the story goes, he wasn’t actually killed with a bow and arrow. Miraculously, he survived being shot with a bow and arrow and was nursed back to health by a Christian woman – then he set out to find the Roman emperor who had him killed for being a Christian. Of course, the emperor saw him and again ordered his death (this time by slaying). Somehow, Renaissance artists preferred the first execution to the second. (It doesn’t take a genius to figure out why.) This image is now on my forearm as one of my favorite tattoos, engraved by the lovely and talented Ruby May Quilter.”

2. Early-Aughts Abercrombie & Fitch

A military marching group walks past a giant Abercrombie & Fitch billboard during the St. Patrick’s Day Parade in New York City in 2005.

“I was raised on all the rich (and, as you now know thanks to good ol’ Sebastian, vaguely homoerotic) images of Catholicism – sweaty six-packs and all that. I’d say the second most important images for my sexual awakening were Abercrombie & Fitch shopping bags and catalogs. In a weird way, Abercrombie’s print editions were sort of a modern version of Physique Pictorial – selling (very effectively) homoeroticism by showing muscular men in distinctly masculine environments like locker rooms and sporting events.

“In fashion, nudity has long been used as an effective way to sell expensive clothing and accessories, and Abercrombie in some ways stepped into the legacy of brands like Dolce & Gabbana and Calvin Klein. However, because it was a mall brand, it also had a grip on the psyche of suburban teenagers – a psyche that perpetuated the notion of beauty as thin (for women) and muscular (for men), and that was predominantly white. The obsession I had with Abercrombie was absolutely toxic, from the way I squeezed into XS polo shirts that never fit to the body ideals I set for myself but would never achieve. When my parents refused to out me to my other friends and family, I responded by creating a collage of Abercrombie models in Microsoft Paint and posting it as the background to my Myspace page. (They were not amused.)

“High-fashion photographer Bruce Weber, long synonymous with iconic American black-and-white images, was responsible for many of the most famous Abercrombie shoots. Decades after those images first surfaced, many models came forward accusing him of sexual harassment and assault. Weber only settled a lawsuit filed by several male models this August, pleading not guilty. It’s really hard to grasp the legacy those images left, what they stood for, and how they still resonate – for some of us in our psyche and for others of us in much more tangible ways.”

3. Jennifer Aniston’s Cover of Vanity Fair

“The first tabloid story I really followed was Brad, Angelina and Jennifer Aniston. I was totally in love with Jen from Friends, but then I came to love Angelina Jolie during Mr. and Mrs. Smith (and if I’m honest, Brad Pitt in that movie was the mood board for my current haircut). The summer I came out, I saw her Vanity Fair cover on the newsstand and it quickly became the first magazine article I ever read.

“The styling and imagery were, of course, genius. Jen in a crisp white shirt – free of fashion pretension, but still classic, casual and beautiful. With her mop of hair, light tan, and fresh makeup, she looked like she’d just returned from vacation. Perhaps, in a way, she was. In a way, it’s unfortunate that this image is also part of my imagination and upbringing – these photos were taken by Mario Testino, who (like Weber) has been accused of sexual assault by some of his protagonists.

“More than the visuals, though, the profile was incredible-the access, the openness, the description of their falling-apart love lives and their willingness to keep it all moving. That’s when I first realized that journalism isn’t just a newspaper, and that you can really tell stories better if you know what visual elements to include to really build your narrative. I finished the profile and flipped through the rest of that issue of Vanity Fair and decided that maybe I wanted to work in magazines. This was, I thought (perhaps very naively), a much more hospitable career for gay people than my original dream of becoming a lawyer.”

4. Vogue’s May 2009 issue featuring Model as Muse

“After Vanity Fair, I started reading Vogue pretty religiously. There was an issue – which I haven’t been able to find since – where Anna Wintour, the editor-in-chief, talked about marriage equality. At the time, I attended a Catholic school and struggled with the idea that I was a sinner and shouldn’t get married or have sex. Reading about other gay people in black and white – especially those who were successful in the fashion industry – had a huge impact. When it came time to decide on college, I was clear: I wanted to go to NYU and I wanted to intern at Vogue. (Both would later come true).

“The issue shown here is one of my favorites from Vogue – when I read about the Model as Muse exhibit, my middle school friend convinced me that we needed to take a road trip to New York to see it. Her mom agreed to drive us, and so I went to the Met for the first time. I never dreamed I’d be walking the Met Gala red carpet some eight years later – as Teen Vogue’s chief content officer.”

5. Tyler Mitchell’s March for Our Lives Covers at Teen Vogue

“We did a lot of important work at Teen Vogue, but the most intense chapter of my career there was the 2018 March for Our Lives. For years, we covered school shootings, the impact on kids’ mental health, and what kind of gun activism was happening on the ground in different places across the country. Parkland was a turning point – a turning point marked very clearly by young people like Sarah Chadwick, Jaclyn Corin and X González, but also by activists like Nza-Ari Khepra, who had lost her boyfriend years earlier in a shooting in Chicago. Samhita Mukhopadhyay, a longtime feminist blogger, journalist and author, had just joined Teen Vogue as managing editor and worked with our politics editor Alli Maloney to shape the coverage and find other youth activists for casting.

“The covers were the most popular we had ever published digitally, and they were photographed by Tyler Mitchell, who (later in the year) would make history. One of them, unfortunately, was Photoshopped by right-wing trolls. The video of this cover shows Emma tearing up a target paper – a statement that children are not targets, but are being made out to be by apathetic government officials. The target paper was changed to the Constitution, Emma’s skin was lightened, and other changes were made to the image. The fake image spread like a virus, and I had to appear on Good Morning America to defend it.

“Sometime before Them launched and while still at Teen Vogue, I joined the Allure team for about a year to manage digital editorial and strategy. I started my editorial career in the beauty department and never stopped being deeply involved in beauty – even though my interests took on a much broader scope as I got older. I was honored to work for Allure and, most importantly, to pitch my ideas to then-Editor-in-Chief Michelle Lee, the first woman of color to head the magazine.

“Before this issue came about, there was a lot of talk on the internet about terms like ‘bikini body’ – these seemingly innocuous and even cute terms that we just accept as typical, but that actually create norms or expectations that are harmful to how we see ourselves (and how others see us). I feel like we could say the same thing about “anti-aging.” Why do we want to be against a process that is inevitable and even natural? Why are we marketed to fight or combat aging and thus capitalize on insecurities? And what is it about anti-aging that seems to focus so obsessively on women who age “poorly” as opposed to men who supposedly age “better”?

“My suggestion to Michelle was that Allure banish the term ‘anti-aging’ from its editorial, but also that the magazine issue a call to industry leaders to do the same. That was basically all I could contribute, too. Michelle (along with Marie Suter, the magazine’s creative director, Jenny Bailly, the beauty director, and Danielle Pergament, the executive editor) then created a really impressive and comprehensive issue that destigmatized aging while providing readers with intelligent and honest information about products and procedures they might be interested in. Helen Mirren was great casting for the cover, and I believe she was followed the next year by the iconic Angela Bassett.

“Looking back on it a few years later, I have a lot of thoughts about that work – especially about whether using different language or terminology actually helped change the way we talk or think about aging, or about how women are pressured to age ‘gracefully’ instead of just accepting who they are. I also wonder if it can be truly authentic, since it’s just a reframing of the way we sell products to people, rather than a comprehensive critique of shame as a marketing tactic. However, I think it’s great that Allure always offers smart and well-researched options for people looking for a product or treatment – and I think the gesture and the magazine’s many efforts (led by Michelle and now continued by Jessica Cruel) to diversify its covers and cast are important and positive steps toward better reflecting what beauty really is.”

7. Out Magazine, The Women & Nonbinary Femmes Issue

“This is my favorite image and my favorite cover that I’ve helped create in my entire career-which is a bit ironic considering that it was really a collaborative effort between Janet Mock (who guest edited the issue and helped cast and idea the entire cover shoot), Raquel Willis (this was her first issue as managing editor at Out, and she worked with Janet on all the details) and Mickalene Thomas, the artist. This issue was the first time in Out’s nearly 30-year history that there were no men on a single page in the bylines, photos, or credits. It was only our second issue with my team at Out-the most diverse team ever to work for the magazine-and it may truly have been our best. (I’m sure my former colleagues will be arguing with me via text message when they see this, and I can’t wait!)

“Pictured here is Stonewall veteran Miss Major, a black trans woman who was in the 1969 uprising. At her feet is Tourmaline, the artist who helped bring Marsha P. Johnson’s legacy to the forefront of our cultural consciousness and celebration in recent years. (Tourmaline’s artwork has since been acquired by some of New York City’s most important museums.) This issue came out in early 2019, the 50th anniversary of the Stonewall Uprising, and the fact that an entire page was dedicated to black activists and artists (including Barbara Smith of the Combahee River Collective, Alicia Garza, and Charlene Carruthers) was a really powerful statement. In the years since that issue came out, we’ve seen Thomas’ portraits of Miss Major and Tourmaline from that issue at protests and parades-that’s the most beautiful sentiment of all.”

8. The 2019 Out 100: The Trans Obituaries Project

“Just before we started work on Out 100, Out magazine’s flagship franchise, we were faced with layoffs and budget cuts, which basically meant we were working with the least resources for the franchise in recent memory.

“When we started working on Out 100, we all knew that the proverbial plug could be pulled on our project at any time. Raquel, our managing editor, made it her mission to create something she was really proud of. The Trans Obituaries Project, a GLAAD Award-winning feature, began with a profile of Layleen Cubilette-Polanco, an African-Latino trans woman who died in solitary confinement at Rikers Island. Layleen’s death sparked activism across New York, drawing attention to the epidemic of violence against trans women of color and also whetting the appetite to close Rikers (and abolish prisons more generally). Raquel followed Layleen’s profile with obituaries for each of the trans women of color we lost in 2019, all of whom were part of the Out 100, and a framework explaining how to end this systemic, cultural, and direct violence.

The cover photo, photographed by Elliott Jerome Brown Jr, shows Layleen’s mother looking at a portrait of her deceased daughter. It’s a powerful photograph that captures the seriousness of this family’s grief, but also reminds us how much Layleen was (and still is) loved by her family.”

9. Out’s Boot Licking Shoot

“I’ll be honest with you: I was terrified to show this photo shoot in the press. But after visiting all the fashion weeks for the first time (i.e. Milan, London, Paris and New York), my fashion director Yashua Simmons convinced me that we should do a fetish shoot. Leather was ubiquitous on the runways for men, and it all seemed a little too…. fetishistic.

“It’s funny, because in European magazines we usually see hypersexualized photo shoots, often winking at homoeroticism without actually going that far. There was a certain legacy of respectability and sexuality that we struggled with at Out, and some members of our team (including writer Mikelle Street) felt strongly that we needed to include the fetish and leather communities more holistically in our coverage. So instead of models, the team cast people from the community, and Yashua sourced leather from all sorts of high-fashion designers. We had a porn star spitting on a boot with his tongue, men sniffing each other’s armpits, and leather daddies posing in all their glory.

“It’s hardly the most revolutionary thing we’ve ever done, but looking back, I appreciate that our team was always able to find room for pleasure-especially ‘deviant’ pleasure-in the midst of all the other work we were doing. Above all, I think the photos are sexy and dignified while still feeling like art, which is absolutely the result of a wonderful collaboration between Hao Zeng and Yashua.”

10. The Rider-Waite Tarot Deck

“During the pandemic, I felt lost in a way I didn’t even know I could. I was kind of trapped in this weird purgatory (there it is again, Catholicism) and was unsure whether to throw myself back into a job or keep hoping I’d find a whole new path. Around Christmas, my friend Tourmaline sent me the Rider-Waite Tarot deck and Rachel Pollack’s book Seventy-Eight Degrees of Wisdom, and I spent two full weeks completely immersed in the pages. When I was younger, I was told that things like the tarot or astrology were heretical and in some cases the work of the devil. Unwrapping the deck and the book felt strange, like I was breaking a rule from my childhood that I’ve kept into adulthood.

“It was the Tarot that I consulted when the prospect of studying theology first landed on my desk in December (via my friend, the poet Cleo Wade). I received many different cards that felt like good signs for an application – for example, the Chariot and the Three of Wands. I sent in my application and promised myself that I would try to forget about it until the decisions came in, which was March 15. One morning in early March, when I was doing my daily draw, I drew a card I had never drawn before: the Hierophant. The card shows a priest sitting on a throne, with two followers on either side. Its meanings suggest orthodoxy, churches, and institutions of higher learning. That’s strange,” I said to myself. I wasn’t supposed to hear from Harvard for another two weeks. I wondered if something was wrong with my application or my transcript, so I flipped open my laptop and checked my email. There, waiting for me, was my acceptance letter. I’m sure a lot of people think I’m crazy or say it was just a coincidence. Lately, I’ve realized that I’d rather live my life believing that there’s more to all of this than just a bunch of happy coincidences or luck. I would like to believe that there is more.

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