For the first time in a decade, Vanity Fair has dropped its best-dressed list—and the 2026 lineup is anything but predictable. While Hollywood A-listers and global pop stars dominate the 70-name roster, one unexpected figure has crashed the party: Pope Leo XIV. The 70-year-old head of the Catholic Church has been hailed for taking papal style “to heavenly heights,” and his secret weapon? A pair of retro Nike trainers.
This isn’t your grandma’s Vatican wardrobe. The Chicago-born pontiff is rewriting the rules of ecclesiastical fashion, blending bespoke vestments with vintage accessories and a distinctly streetwise edge. From battered briefcases to baseball caps, Leo’s look is resonating far beyond the pews—especially with Gen Z.
The Look: Holy Drip or Divine Intervention?
Leo’s most viral moment came last May, when a still from the Vatican-produced documentary Leone a Roma showed him rocking white cassock and Nike sneakers. The internet collectively lost it—many assumed it was AI-generated, recalling the infamous Balenciaga puffer jacket Pope Francis meme. But no, this was real life. Trainer heads quickly ID’d the kicks as a discontinued 1970s retro tennis shoe, and the discourse exploded.
Key Elements of the Leo Aesthetic
- Nike trainers over traditional red papal slippers
- Simple black oxfords for formal moments
- Discontinued Swiss quartz watch—no flashy bling
- Battered leather briefcase he carries himself
- White Sox baseball cap popped over his zucchetto (June 2025, St. Peter’s Square)
For high-profile ceremonies, he turns to Italian designer Filippo Sorcinelli, who also dressed Popes Benedict XVI and Francis. The mix of high and low, sacred and street, is what makes Leo’s style so compelling.
Why Gen Z Is Obsessed
The Catholic Church has always mastered symbolism, but Leo’s approach feels refreshingly modern. His criticism of AI, calls for peace, and active Instagram presence speak directly to younger generations. Professor Robert Orsi of Northwestern University notes, “The world’s embrace of this pope has been stunning to me.” He points to the trainers as a symbol: “A sportiness? A familiarity with track and field, basketball courts, running? They signal that he is approachable, like a good coach, and also humble.”
The Vatican vs. The Runway
This isn’t the first time the papacy has intersected with fashion. From Christian Lacroix’s ecclesiastical riffing in the ’80s to the Met’s Heavenly Bodies exhibition in 2018, the Vatican has long been a muse. But Leo is different—he’s not just inspiring designers; he’s a bona fide style icon in his own right.
| Pope Leo XIV | Traditional Papal Style |
|---|---|
| Nike retro trainers | Red leather slippers |
| Battered briefcase | Ornate staff |
| White Sox cap | Fur-trimmed camauro |
| Quartz watch | Gold jewelry |
| Vintage accessories | Tailored vestments only |
Vanity Fair’s style correspondent José Criales-Unzueta, who helped compile the list, praised the “innate Americanness” of Leo’s dressing. The pope landed in the “originals” category—alongside Spike Lee, Björk, and Rosalía—for being “outlandish and innovative” with “a singular point of view.”
From Viral Moment to Fashion Staple
What started as a viral documentary still has snowballed into a full-blown fashion movement. By late 2025, Leo was featured in Vogue’s best-dressed list alongside A$AP Rocky and Bad Bunny, and the New York Times named him one of its 67 Most Stylish People. Esquire called it “a papal flex.” The internet coined it “holy drip.”
Criales-Unzueta sees this as bigger than one man’s wardrobe: “The list is an opportunity to showcase the way fashion and style are deeply embedded in culture and society. Style, good style, is a practice that is not reserved for celebrities or their stylists.”
What It Means for Streetwear
Leo’s rise signals a broader shift—high-fashion gatekeeping is crumbling. A 70-year-old pontiff in retro Nikes is proof that personal style trumps brand collabs. Carol Richardson, professor of early modern art history at the University of Edinburgh, says Leo and his team are “very savvy.” They know the optics. They’re leaning in.
The result? A pope who looks like he could roll up to a flea market or a Vatican summit with equal ease. That’s the Y2K-era energy—mixing luxury with thrift, sacred with street, and making it all look effortless.
FAQ
Is Pope Leo XIV actually wearing Nike trainers?
Yes. He was first spotted in them in May 2025 during a Vatican-produced documentary. The sneakers are a discontinued retro tennis style from the 1970s, instantly identified by eagle-eyed trainer fans.
Why is Pope Leo XIV considered a style icon?
He blends traditional papal vestments with accessible, vintage-inspired accessories—like battered briefcases, simple watches, and baseball caps—creating a uniquely humble yet modern aesthetic that resonates with younger generations.
Did Pope Francis wear Balenciaga?
No. That viral image was AI-generated and is now considered one of the first major AI misinformation cases. Pope Leo’s Nike moment, however, is completely real.
What is the “originals” category in Vanity Fair’s list?
It’s a division for individuals praised as “the most outlandish and innovative dressers” with a singular point of view. Leo shares it with Spike Lee, Björk, and Rosalía.
Will this influence streetwear trends?
It already has. The “holy drip” aesthetic—mixing formal with sporty, vintage with modern—is a natural fit for Y2K-inspired fashion. If a pope can rock retro Nikes with a cassock, anything goes.
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