Style Across The Aisle
The spotlight cuts through the marbled hall of Surrogate’s Court at New York Fashion Week’s Style Across the Aisle, catching an unlikely runway star mid-stride. Instead of a measured walk, he drops into a full break-dance, spinning across the stage in slick black leather by Harlem designer Mel Maxi, a protégé of Dapper Dan. The crowd gasps, hands flying to mouths, as disbelief ripples down the front row. Candace Bushnell claps wildly, fashion founders lean forward, and applause fills the gilded room. From the mic, a voice cuts through the chaos: “You didn’t see that coming, did you?”
It’s Skye Ostreicher, the woman everyone simply calls Skye, and the architect of the night. For those who thought politics was too heavy, too boring, too divisive for the runway, Skye proved otherwise. The event, only in its second season, has become one of Fashion Week’s most surprising tickets. Its secret is Skye’s alchemy. Politics, it turns out, can be not just surprising but fun. And making politics fun, against all odds, is Skye’s signature.
Style Across the Aisle is her boldest experiment yet: a runway where leaders model designs by creators from their own neighborhoods. “These are elected officials,” Skye teased from the mic. “They’re supposed to be role models. Tonight, they’re showing real model behavior.” The premise is deceptively simple: pair a public figure with a local designer and let style tell the story. But the results have been electric.
Andy Yu, a designer with a cult following and friends like Martha Stewart, crafted a tailored blazer embroidered with delicate fly-fishing flies, an ode to his model’s boyhood in the Adirondacks. Queens-based Soara, founded by Surya Garg, blended South Asian craftsmanship with sleek modern cuts, her designs flowing as naturally on the runway as they do in Jackson Heights. Kate McGuire of Converted Closet, whose upcycled couture once dressed Sarah Jessica Parker on Sex and the City, turned vintage textiles into a floral gown that stunned precisely because it felt both timeless and fresh. And Harlem’s Mel Maxi, with roots in Dapper Dan’s bold aesthetic, closed the night with a leather suit that became the talk of the town after his model’s surprise break-dance brought the house down.
The brilliance of the show lies in borough-to-borough DNA. Each garment carries the imprint of a district, a culture, a lived experience. In that room, filled with designers, editors, donors, and voters, the labels of “politician” or “power broker” disappeared. What remained was laughter, surprise, and the undeniable truth that clothes can reveal the human side better than speeches ever could.
Skye likes to say she practices “human chemistry.” She studied actual chemistry at the University of Miami, planning on medical school, until a talk by university president Donna Shalala, joined by President Bill Clinton, cracked the door to politics. Shalala’s story about serving as designated survivor during a State of the Union revealed the hidden stakes of leadership. Skye was hooked not by policy, but by people. She accelerated her studies, graduated early, and earned a master’s degree in public health and public policy.
In The Room Media
Her career, however, was never a straight line. In 2020 she joined Mike Bloomberg’s presidential campaign, only to watch it collapse days before COVID shut New York down. “I was unemployed and locked inside,” she recalls. Undaunted, she began calling everyone she knew, hosting raw Zoom conversations that grew into her digital interview series Political Personalities with Skye. A media company soon hired her to lead digital coverage, but in 2023 it cut the division. Instead of retreating, Skye doubled down. With strategist Carolyn Vaeth, she turned a sketch of an idea into Style Across the Aisle and founded In The Room Media, her “media-first advocacy” shop.
“People didn’t know what to make of me,” she says. “I never used my press pass for gotcha questions. I used it to elevate the positive.” That instinct to see the person rather than the position is what now defines her empire.
For Skye, fashion isn’t about fabric alone; it’s a Trojan horse for empathy. Style Across the Aisle is spectacle with substance, showing how couture can collapse walls. One minute a conservative lawmaker and a progressive council member are passing each other on the catwalk. The next minute, they are laughing together in shared fabric, their differences softened by style “Clothes disarm people,” Skye explains. “They remind us of what we share, not just what sets us apart.”
It is a strategy she applies everywhere. Her interviews have put officials in garbage trucks at 4 a.m., Cessnas above Manhattan, and tattoo chairs beside her. Each scenario strips away talking points and makes room for real connection. To Skye, it is all one project: changing the chemistry of power by changing the setting.
Community & Jewish Philanthropy Philanthropy is woven into Style Across the Aisle, each year spotlighting a nonprofit partner whose mission expands the runway beyond fashion. This season, the spotlight fell on Witness to Mass Incarceration’s Art of Tailoring program, which works with formerly incarcerated and homeless youth. The program’s three tracks—entrepreneurial training, essential tailoring skills, and small-business expansion—give participants practical expertise and a platform for reinvention. Their creations, modeled by Queens leaders, carried not just crisp lines and bold cuts but also a message: fashion can be a second chance, sewn with resilience and ambition.
Beyond the runway, Skye’s commitments reflect the same philosophy of humanizing what too often feels divisive. She is deeply involved with Jewish organizations including the Jewish Community Relations Council, HMTCLI, and UJA, where she lends her network and media savvy to advocacy and cultural projects. At a Long Island synagogue this spring, she spoke on Holocaust Remembrance Day, warning of the dangers of labels. Just as she works to peel away “Democrat” or “Republican” in politics, she urged the audience to see beyond the label “Jew,” a word that still too often carries prejudice.
“People connect when you show the person, not the category,” she says. That ability, whether on a runway, in a civic setting, or at a synagogue podium, is what makes Skye’s chemistry unique. She designs not just rooms but moments of recognition, turning style into a universal language of connection.
Building Connections.
If Skye expands Style Across the Aisle to Miami or Chicago, she will not just be exporting a fashion show. She will be exporting a philosophy: that power can be playful, that leaders can be relatable, that couture can stitch together divides speeches never could.
It is politics as theater, but with texture and sequins instead of slogans. It is culture reimagined as collaboration, stitched neighborhood by neighborhood. And it leaves the audience—designers, editors, donors, and voters alike—wanting more.
With two master’s degrees, a Fashion Week franchise, and a Rolodex of New York’s cultural power players, Skye Ostreicher is only beginning. Political Personalities will keep peeling back facades. In The Room will keep building connections. And Style Across the Aisle will keep strutting forward, proving that fashion and humanity share more than a spotlight: they share the power to transform.
New York has never lacked for parties or politics. Skye Ostreicher is the first to make them indistinguishable, and to leave the city wondering which room or runway she will unlock next.
Instagram: @thepoliticalpersonality
