Style Across the Aisle — How Skye Ostreicher's Bipartisan Fashion Show Came to Life

At a moment when American politics often feels more like trench warfare than public service, Skye Ostreicher is betting on fashion to stitch together something different: connection.

This September, more than 30 elected officials—from former governors to current council members—will trade the chamber for the catwalk at the second annual Style Across the Aisle, a bipartisan fashion show Ostreicher dreamed up to humanize politics and uplift local designers. The event, set for September 10 at the historic New York County Surrogate’s Court, pairs lawmakers with designers from their districts in what Ostreicher calls “a runway for the future of New York City.”

“Politics is something people frown upon,” Ostreicher said in an interview. “Government works slow, there’s bureaucracy, and people roll their eyes. I wanted to flip that narrative—show people another side of their leaders, one that makes you smile.”

The show made its debut last year at Gracie Mansion, the mayor’s official residence, where 26 officials walked in looks created by 30 designers. Tickets sold out, 200 guests filled the lawn, and the night raised $75,000 with all proceeds for charity. Ostreicher and her volunteer steering committee knew they had tapped into something unique.

This year, the production is scaling up. Surrogate’s Court, with its soaring ceilings and marble colonnades, will serve as the backdrop for a guest list that has already doubled to 300. Among those confirmed to strut are former governors Andrew Cuomo and David Paterson, Council Majority Leader Amanda Farias, and Council Minority Leader Joann Ariola. Mayor Eric Adams is expected to deliver remarks.

“I think the idea of Governor Cuomo doing a runway show is fantastic,” Ostreicher laughed. “It softens him, makes him human in a different way. That’s really the goal—humanizing the people we usually only see behind a podium.”

The project is as much about designers as it is about politics. Every official is paired with a creator from their own community, a deliberate effort to spotlight New York’s fashion economy at a hyper-local level.

Last year, Inspector General Lucy Lang walked in a look designed by a formerly incarcerated tailor—an idea Ostreicher pushed for despite the logistical hurdles of bringing such a designer into Gracie Mansion. This year, the partnership deepens: the show’s nonprofit beneficiary is Witness to Mass Incarceration, a Queens-based group whose Art of Tailoring program trains justice-impacted youth in design and entrepreneurship.

“They’re taking young people who’ve been incarcerated and teaching them the art of tailoring,” Ostreicher explained. “That’s not just fashion, it’s new business, it’s manufacturing, it’s confidence. It’s giving people a second chance.”

One of those designs will be worn by Assemblymember Eddie Gibbs, the first formerly incarcerated person elected to the New York State Legislature. Councilmember Julie Won and Queens Borough President Donovan Richards will also wear custom creations from the program.

For Ostreicher, persuading politicians to walk the runway wasn’t as hard as it might sound. “When I pitch it, people smile immediately,” she said. “It’s bipartisan, it’s fun, and it’s about local pride. Who doesn’t want to be part of that?”

The ease of her ask is rooted in years of relationship-building. Ostreicher started her career in politics after an unlikely pivot: she had been a pre-med student on scholarship at the University of Miami when then-president Donna Shalala invited Bill Clinton to lecture her class. Listening to their stories, Ostreicher realized she wanted to pursue health policy rather than medicine.

She earned two master’s degrees—one in public health, another in public policy—before working on campaigns, including a stint as regional director on Mike Bloomberg’s 2020 presidential bid. When the pandemic shut down New York days after that campaign ended, she turned to Zoom and launched a video interview series with local leaders. Over time she built a reputation as a friendly, accessible media personality who could draw politicians out of their talking points.

“I never ask hardball questions,” she said. “I just want people to connect as humans.”

Her show Political Personalities with Skye became a platform for just that, taking viewers inside the lives of legislators—flying in planes with hobbyist senators, joining sanitation workers at dawn, even celebrating with their families and pets.

So when Ostreicher calls with another “wacky idea,” as she puts it, officials trust her. “They know it’s going to make them look good,” she said.

This year’s sponsors reflect that trust. Airbnb has signed on as the largest backer, joined by Uber, EmblemHealth, Aeon Nexus Corporation, and other national names, alongside local partners like Beauty Social Salon and Rethink Food, which is supplying 4,000 hors d’oeuvres sourced from neighborhood restaurants.

“It makes me feel great that not only have I built the relationships to bring that kind of support, but also that these brands see the value in something bipartisan and positive,” Ostreicher said.

Her long-term vision goes beyond New York. She has trademarked Style Across the Aisle and hopes to license the format to other cities. “Why not do this in Miami, in L.A., in Chicago?” she asked. “It’s a way to elevate local businesses, bring communities together, and show that fashion can bridge divides where politics can’t.”

As Ostreicher reflects on her path—from a pre-med student inspired by a chance encounter with a president, to a public relations professional creating one of Fashion Week’s most surprising shows—she keeps returning to the same word: humanize.

“Fashion is universal,” she said. “We can all agree when someone looks great. On the runway, it doesn’t matter if you’re a Democrat or Republican. It’s about bonding, about celebrating what makes New York special.”

In a season known for spectacle, Style Across the Aisle offers something deeper: a reminder that even in polarized times, a shared runway can be a common ground.

To learn more and purchase tickets visit, www.styleacrosstheaisle.com