These Are The Iconic Magazine Covers That Defined A Teen Vogue Editor’s Career

Phillip Picardi, the former Teen Vogue editor and Them founder, on religious iconography, queer representation, and Abercrombie & Fitch.

When I was a teenager, magazines were everywhere — the doctor’s office, the magazine aisle at the grocery store where my mom shopped, piled up on the babysitter’s couch. The really good issues were passed around by the parents in my neighborhood. I was struck by the images on the covers, but only in the very basic sense that I wanted to understand what was going on in the heads of the teens and celebrities in them. How was the magazine sausage made? That would remain a mystery to me for decades.

Around the same time, in Boston, Phillip Picardi was thinking about magazines as well. He would go on to have the kind of magazine career that kids can only dream of — he worked at Teen Vogue during its most political days, founded the LGBTQ-lensed Them magazine, served as the editor-in-chief of Out magazine, and worked for Refinery29 and Allure. Now, Picardi is back to his journalism roots and working for himself: He’s a master’s student at Harvard Divinity School and runs a popular newsletter, "Religiously Blonde," and podcast, Unholier Than Thou and look at the intersection of religion, spirituality, and culture. We spoke with him about 10 images that inspired the trajectory of his career (and the tarot).

1. Saint Sebastian

“Of all the saints, Sebastian seems to have captured the gay imagination the most. Nearly all art historical depictions show him as a lithe young twink, bound to a tree, being — ahem — penetrated by a whole bunch of arrows. It took me quite a few years into young adulthood to realize why I was so drawn to these images. (Please don’t worry; it doesn’t have to do with the blood.) Funnily enough, St. Sebastian may have been a martyr, but as the story goes, he wasn’t actually killed by bow and arrow. Miraculously, he survived the bow and arrows and was nursed back to health by a Christian woman — then, he went in search of the Roman emperor who had ordered him killed due to his Christianity. Naturally, the emperor saw him and, once again, ordered him dead (this time by being clubbed). Somehow, the artists of the Renaissance preferred the first execution to the second. (It doesn’t take a genius to figure out why that might be.) Now, this image lives on my forearm as one of my favorite tattoos, inked by the lovely and talented Ruby May Quilter.”

2. Early-Aughts Abercrombie & Fitch

“I was raised with all the rich (and, as you now know thanks to good ol’ Sebastian, vaguely homoerotic) imagery of Catholicism — sweaty six-packed bodies and all. I’d say the second-most important imagery relating to my sexual awakening were Abercrombie & Fitch shopping bags and catalogs. In some weird way, Abercrombie’s printed editions were like some sort of modern version of Physique Pictorial — selling (very effectively) homoeroticism by placing beefcake men in distinctly masculine environments, like locker rooms and sporting activities.

“Fashion has long used nudity as an effective mechanism for selling expensive clothing and accessories, and Abercrombie was, in a way, following in the legacy of brands like Dolce & Gabbana and Calvin Klein. But, being a mall brand, it also held a grip over the suburban teenage psyche — one that perpetuated the idea of beauty as thin (for women) and muscular (for men) and was overwhelmingly white. The obsession I had with Abercrombie was utterly toxic, from the way I squeezed into XS polo shirts that never fit to the body ideals I held myself to but would never meet. When my parents refused to let me come out of the closet to my other friends and family, I responded by making a collage of Abercrombie models in Microsoft Paint and then setting it as the background of my Myspace page. (They were not amused.)

“The high-fashion photographer Bruce Weber, long synonymous with iconic American black-and-white imagery, was responsible for many of Abercrombie’s most iconic shoots. Decades after these images first surfaced, many models would come forward to accuse him of sexual harassment and assault. Weber just settled a lawsuit brought by multiple male models in August of this year and did not admit guilt. It is truly hard to come to grips with the legacy these images left behind, what they stood for, and how they still endure — for some of us in our psyches, and for others of us in much more tangible ways.”

3. Jennifer Aniston’s Cover of Vanity Fair

“The first tabloid story I ever really followed was Brad, Angelina, and Jennifer Aniston. I was completely in love with Jen from Friends, but then I came to love Angelina Jolie during Mr. and Mrs. Smith (and, if I’m being 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 was, of course, genius. Jen in a crisp white shirt — free of fashion pretension, but still looking classic, easy, and beautiful. Her bedhead, light suntan, and fresh makeup made her look like she’d just come back from a vacation. Maybe, in a way, she did. It’s unfortunate, in a way, that this image is also a part of my imagination and upbringing — these photos were taken by Mario Testino, who (like Weber) was accused of sexual assault by some of his subjects.

“More than the visuals, though, the profile was incredible — the access, the candor, the description of her romantic life falling apart and her willingness to keep it all moving. It was the first time I realized that journalism wasn’t just a newspaper, and that storytelling could really be amplified when you know what visual elements to incorporate to really build your narrative. I finished the profile and went through the rest of that issue of Vanity Fair and decided that maybe I wanted to work in magazines. It was, I figured (perhaps very naively), a much more hospitable career to gay people than my initial dream of being a lawyer.”

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

“After Vanity Fair, I started reading Vogue fairly religiously. There was one issue — and I haven’t been able to find it since — where Anna Wintour, the editor-in-chief, talked about marriage equality. At the time, I was attending Catholic school and was really grappling with the idea that I was a sinner and shouldn’t get married or have sex. To read in black and white about other gay people — especially folks succeeding in fashion — was massively influential. When it came time to decide where I might want to apply to college, I was crystal clear: I wanted to go to NYU, and I wanted to intern for Vogue. (Both things would later come true.)

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

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 during the March for Our Lives in 2018. For years, we’d been covering school shootings, the effects it had on kids’ mental health, and what kind of gun activism was happening on the ground in different places throughout the country. Parkland was a tipping point — one marked very clearly by vocal young people like Sarah Chadwick, Jaclyn Corin and X González, but one that was also built on by activists like Nza-Ari Khepra, who lost her friend years earlier to a shooting in Chicago. Samhita Mukhopadhyay, a longtime feminist blogger, journalist, and author, had just joined Teen Vogue as our executive editor and teamed up with our politics editor, Alli Maloney, on framing the coverage and identifying other youth activists for the casting.

“The covers were the most popular we’d ever run on digital at the time, and they were lensed by Tyler Mitchell, who would (later that year) make history. One was also, sadly, photoshopped by right-wing trolls. The video of this cover shows Emma ripping up a target paper — a statement that kids were not targets, but were being made out to be by apathetic government officials. They changed the target paper to be the Constitution, lightened Emma’s skin, and made other alterations to the image. The fake image went viral, and I had to go on Good Morning America to defend it."

6. The End of Antiaging for Allure

"At some point before launching Them and while still at Teen Vogue, I joined the team at Allure for about a year to help steer the digital editorial operations and strategy. I started my editorial career in the beauty department, and I truly never stopped caring deeply about beauty — even though my interests took on a much more expansive purview as I got older. It was an honor to work for Allure, and especially to show my ideas to the magazine’s then-EIC, Michelle Lee, who was the first woman of color to lead the publication.

“Before this issue came to fruition, there was a lot of talk online about phrases like ‘bikini body’ — these sort of seemingly innocuous and even cutesy terms we just accept as typical but are actually creating norms or expectations that are harmful to how we view ourselves (and how others view us). I felt like we could argue the same thing about ‘antiaging’: Why do we want to be anti a process that is inevitable, and even natural? Why are we being marketed to combat or fight aging and, thus, capitalizing on insecurities? And what was it about antiaging that seemed to so obsessively focus on women as aging ‘poorly’ versus men, who allegedly ‘age better’?

“My proposal to Michelle was that Allure banish the phrase ‘antiaging’ from its editorial, but also that the magazine would create a call to action for industry leaders to do the same. That was basically the extent of my contribution, though — from there, Michelle (together with Marie Suter, the magazine’s creative director; Jenny Bailly, the beauty director; and Danielle Pergament, the executive editor) created a really stunning and comprehensive issue that worked to destigmatize aging while still allowing readers to have intelligent and honest resources about products and procedures they might be interested in. Helen Mirren was such a great casting for the cover, and I believe she was followed up by the iconic Angela Bassett the next year.

“Looking back on it a few years later, I have a lot of thoughts about this effort — particularly about whether or not the use of different language or terminology actually helped to change the way we talk or think about aging, or the ways in which women are pressured to age ‘gracefully’ rather than just embracing who they are. I also wonder whether or not it can be truly authentic given that it’s just a reframing of how we sell products to people rather than a more full-throated critique of shame as a marketing tactic. However, I love that Allure always provides smart and well-researched options for people looking for a product or a procedure — 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 castings are important and positive strides to help better reflect what beauty really is.”

7. Out Magazine, The Women & Nonbinary Femmes Issue

“This is my favorite image and my favorite cover I’ve ever helped to make happen in my entire career — which is a little bit ironic, considering it really was a joint effort between Janet Mock (who guest-edited the issue and helped cast and ideate this entire cover shoot), Raquel Willis (this was her first issue as executive editor at Out, and she worked with Janet on all its details), and Mickalene Thomas, the fine artist. This issue marked the first time in Out’s nearly 30-year history that men were absent from the bylines, photography, and credits of every single page. It was only our second issue with my team at Out — the most diverse team ever to work for the magazine — and it really may have been our best. (I’m sure my former colleagues will all argue with me about this via text message when they see this, and I can’t wait!)

“Here, you see pictured the Stonewall veteran Miss Major, a Black trans woman who was at the uprising in 1969. At her feet is Tourmaline, the artist who helped to bring Marsha P. Johnson’s legacy towards the forefront of our cultural awareness and celebration in recent years. (Tourmaline’s artwork has since been acquired by some of the most major museums in New York City.) This issue came out at the beginning of 2019, which marked the 50th anniversary of Stonewall, and having a full spread celebrating Black women activists and artists (including Barbara Smith from the Combahee River Collective, Alicia Garza, and Charlene Carruthers) was a really powerful statement. In the years since this came out, we’ve seen Thomas’s portraits of Miss Major and Tourmaline from this issue at protests and parades — the greatest feeling of all.”

8. The 2019 Out 100: The Trans Obituaries Project

"Right before we began work on the Out 100, the most important franchise at Out magazine, we faced layoffs and budget cuts that basically meant we were working with the least resources for the franchise in recent memory.

“It was atop all of our minds when we began the Out 100 that the proverbial plug could be pulled on our project at any minute. Raquel, our executive editor, made it her mission to create something that she was truly proud of. The Trans Obituaries Project, a GLAAD Award–winning feature, opened with a profile of Layleen Cubilette-Polanco, an Afro-Latinx trans woman who died while in solitary confinement at Rikers Island. Layleen’s death prompted activism throughout New York, bringing attention to the epidemic of violence against trans women of color and also stoking the appetite for closing Rikers (and, more broadly, prison abolition). Raquel followed the profile of Layleen with obituaries for each of the trans women of color we lost in 2019, all of whom were a part of the Out 100, and a framework that explains how to end this systemic, cultural, and direct violence.

The cover, shot by Elliott Jerome Brown Jr., shows Layleen’s mother looking at a portrait of her late daughter. It was a powerful photo that captured the solemnity of this family’s grief, but also a reminder of how loved Layleen was (and still is) by her family."

9. Out’s Boot Licking Shoot

“I will be honest with you: I was terrified to run this photo shoot in print. But after my first time going to a full circuit of Fashion Weeks (that means Milan, London, Paris, and New York), my fashion director, Yashua Simmons, convinced me we needed to do a fetish shoot. Leather was all over the men’s runways, and it all seemed a little overtly... fetishistic.

“It’s funny, because we most often see hypersexualized photo shoots in European magazines, and they often wink at homoeroticism without actually going there. There was a certain legacy of respectability and sexuality that we were contending with at Out, and a few members of our team (including the writer Mikelle Street) were adamant that we needed to include the fetish and leather communities in our coverage more holistically. So, instead of models, the team cast folks from the community, and Yashua summoned leather from all sorts of high-fashion designers. We had a porn star spit-shining a boot with his tongue, men sniffing each other’s armpits, and leather daddies posing in all their glory.

“It is hardly the most revolutionary thing we’d ever run, but looking back, I do appreciate that our team was always able to find space for pleasure — especially ‘deviant’ pleasure — amidst all the other work we were doing. Above all, I think the photos are sexy, dignified, and still feel like art, which is absolutely the result of a beautiful 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 that I could. I was kind of caught in this weird purgatory (there’s that Catholicism again) and was unsure if I wanted to jump back into a job or continue hoping that I’d find a brand-new path. Right 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 its 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. Unpacking the deck and the book felt weirdly like betraying some childhood rule that stuck with me into adulthood.

“It was the tarot I consulted when the prospect of divinity school first crossed my desk (via my friend, the poet Cleo Wade) in December. I got a lot of different cards that felt like good signs for an application — the Chariot, for one, and the Three of Wands. I sent in my application and promised myself I’d try and forget about it until decisions came in, which was March 15. One morning in early March, I was doing my daily pull when I drew a card I’d never drawn until then: the Hierophant. The card depicts a priest seated on a throne, two followers on either side of him. Its meanings suggest orthodoxy, churches, and institutions of higher education. ‘That’s weird,’ I said to myself. ‘I’m not supposed to hear from Harvard for another two weeks.’ I wondered if something was wrong with my application or my transcript, so I opened 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 could say it was just a coincidence. Lately, I’ve realized that I prefer to live my life believing that there’s more to all of this than just a bunch of happy coincidences or luck. I’d like to believe there’s something more.”

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