For the first time in a decade, Vanity Fair has unveiled its highly anticipated best-dressed list, and standing among Hollywood royalty, global music icons, and fashion royalty sits an unexpected name: Pope Leo XIV.
The 70-year-old leader of the Catholic Church has earned recognition alongside 69 other individuals for what the magazine describes as taking papal fashion “to heavenly heights.” His unconventional approach to dressing has captured the attention of fashion critics worldwide, transforming him from spiritual leader to unexpected style icon.
“He would be aware of his inclusion on the list,” said Carol Richardson, a professor of early modern art history at the University of Edinburgh. “He and the people surrounding him are very savvy. The majority will think it’s fun. They will like the fact it has been noticed how busy he is, that he has to wear trainers to run around in. That he is working.”
A Chicago Pope, A Global Style Movement
Pope Leo XIV hails from Chicago, and according to Vanity Fair’s style correspondent José Criales-Unzueta, who helped compile the list, that American upbringing shines through in his wardrobe choices. The editorial team was struck by what they described as the “innate Americanness” of his sartorial approach.
Gone are the traditional red papal slippers. In their place, the Chicago-born pontiff opts for simple black Oxford shoes and, most memorably, a pair of Nike trainers. When he was first spotted wearing the athletic shoes in a still from Leone a Roma—a Vatican-produced documentary retracing his time in Rome before his elevation to the papacy—the image went viral. Many initially mistook it for a hoax, recalling the infamous AI-generated image of Pope Francis sporting an oversized Balenciaga puffer jacket.
“What a papal flex,” declared Esquire at the time, while social media users quickly christened his distinctive style as “holy drip.”
Train enthusiasts were swift to identify the pontiff’s Nikes as a discontinued retro tennis-style shoe originally sold in the 1970s. The detail only deepened the fascination.
From Streetwear to Sacred Vestments
The pope’s fashion repertoire extends far beyond athletic footwear. At a general audience in June 2025, he notably perched a Chicago White Sox baseball cap atop his papal skullcap in St Peter’s Square—a bold fusion of sports allegiance and sacred duty that sent ripples through both religious and fashion circles.
He carries his own battered briefcase, wears a discontinued Swiss-made quartz watch, and for more formal occasions, turns to Italian designer Filippo Sorcinelli, who previously created liturgical vestments for Popes Benedict XVI and Francis. This blend of the worn and the bespoke, the athletic and the ecclesiastical, has carved out a unique style niche for the pontiff.
By the end of 2025, his fashion momentum showed no signs of slowing. He found himself featured alongside A$AP Rocky and Bad Bunny in Vogue’s best-dressed list, while The New York Times recognised him among its 67 Most Stylish People of the year.
Connecting with a New Generation
The Catholic Church, with its long history of mastering symbolism and optics, appears to be experiencing a renaissance driven by Generation Z. Robert Orsi, a professor of religious studies at Northwestern University in Illinois, said he has been contemplating what the trainers truly represent.
“A sportiness? A familiarity with track and field, basketball courts, running?” he mused. “For me, it’s a lightness on his feet, a readiness to move quickly to where he is needed the most. They signal that he is approachable, like a good coach, and also humble.”
The timing of Leo’s fashion ascendancy coincides with broader cultural conversations. His outspoken criticism of artificial intelligence and impassioned calls for peace have resonated deeply with younger generations, adding substance to his style story.
Vanity Fair’s global editorial director Mark Guiducci has described the publication as “a magazine about personalities” that feels “like the pantheon.” For Leo’s team, inclusion in such rarefied company aligns with the papacy’s own strategic positioning as a modern, relevant institution.
“The world’s embrace of this pope has been stunning to me,” Orsi noted.
A Singular Vision
On Vanity Fair’s list, Pope Leo XIV appears in the “originals” division—a category reserved for individuals commended as “the most outlandish and innovative dressers” with “a singular point of view.” He joins an eclectic roster including filmmaker Spike Lee and singers Björk and Rosalía.
The broader appeal of the papacy to fashion circles is not new. From Christian Lacroix’s ecclesiastical designs in the 1980s to the Metropolitan Museum’s celebrated Heavenly Bodies exhibition in 2018, the Vatican has long served as a source of inspiration. Crucifixes and depictions of Christ have appeared on recent catwalks, underscoring the enduring fascination.
Criales-Unzueta explained the attraction: “There is so much to take in and so much to find inspiration in.”
He described the best-dressed list as “an opportunity to showcase the way fashion and style are deeply embedded in culture and society” and that “style, good style, is a practice that is not reserved for celebrities or their stylists.”
Why it Matters
Pope Leo XIV’s inclusion on Vanity Fair’s best-dressed list marks a significant cultural moment that extends well beyond fashion trivialities. In an era of declining religious participation and institutional distrust, particularly among younger generations, the pontiff’s unexpected style iconography serves as a powerful communication tool. His willingness to embrace accessible footwear and beloved sports teams signals a papacy willing to meet people where they are, transforming centuries-old traditions into something relatable without diminishing their sacred weight. Whether one views his fashion choices as genuine authenticity, calculated public relations, or some blend of both, the conversation they generate keeps the Catholic Church relevant in spaces it might otherwise never reach. The Vatican has always understood the propaganda value of image; Leo XIV simply speaks the language of 2026.