It didn’t take long for someone to break the ice. “Nervous about Tuesday?” joked New York Senator Kirsten Gillibrand in a warm up speech that set the tone for the creative directors, retailers, editors, executives, celebrities, and socialites. The awkward giggles and deflated sighs in response indicated that, yes, everyone was nervous about Tuesday.

At the hotel where Chavarria and his guests were prepping, you could feel the excitement tinged with an unmistakable edge, and not just because a few outfits were still en route, stuck in traffic. Chavarria’s father hails from Mexico, and as his brand has grown in visibility the designer’s work has become more personal—and more political. There’s a critique inherent in his casting, which turns mustachioed Romeos and tattooed tough-guys from his creative community into fashion faces, ones you don’t see fronting other brands. And there’s a palpable sense of pride in his exploration of modern Latinidad style, weaving elements of Chicano and cholo fashion trends—flowy zoot suits, three-quarter-length trousers, oversized flannels, flat brims—with preppy archetypes.

Of his fellow menswear nominees, which included Thom Browne, Mike Amiri, Emily Adams Bode Aujla, and Todd Snyder, Chavarria is the only one who designs with the heart of an activist. In September, as the Trump campaign’s anti-immigrant rhetoric hit a once-unthinkable register, Chavarria sharpened his message. In an abandoned Wall Street bank, Chavarria hung an enormous American flag over the catwalk and sent out sweatshirts emblazoned with the eagle logo of the United Farm Workers, a nod to the line of migrant workers in his family, and the sartorial equivalent of a raised fist. (Chavarria lore has it that Cesar Chavez once dropped by for coffee at their house in Huron, California.)

Chavarria and his crew are distinctly aware of what’s on the line next week. In the hotel, I found Top Gun: Maverick ace Danny Ramirez waiting to change into a custom velvet lounge suit. “It has felt like the longest 24 hours,” Ramirez said, a hint of exasperation in his voice. Ramirez was referring to the racist rhetoric that billowed out of Donald Trump’s Sunday night rally at Madison Square Garden, where the comedian Tony Hinchcliffe made derogatory remarks about Puerto Rico that were still ricocheting around social media. “It’s a joke in its intended terms,” said Ramirez, who is of Mexican and Colombian descent, “but exchange Puerto Rico with Mexico, with Colombia, and it’s how a lot of people feel about us.”

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