Style Beyond the Aisle — The Story of Skye Ostreicher's Bipartisan Fashion Show

A New Approach to Politics Through Fashion

In a political climate often marked by division and conflict, Skye Ostreicher is using fashion as a tool to bring people together. Her initiative, Style Across the Aisle, is a bipartisan fashion show that aims to humanize politics and celebrate local designers. This September, over 30 elected officials will trade their legislative roles for the runway at the second annual event.

The event, set for September 10 at the historic New York County Surrogate’s Court, pairs lawmakers with designers from their districts. Ostreicher describes it as “a runway for the future of New York City.” The goal is to shift the perception of politics from something people frown upon to an engaging and positive experience.

Last year’s debut at Gracie Mansion was a success, with 26 officials walking in looks created by 30 designers. Tickets sold out, and the event raised $75,000 for charity. This year, the production is scaling up, with a guest list that has doubled to 300. Among those confirmed are former governors Andrew Cuomo and David Paterson, Council Majority Leader Amanda Farias, and Council Minority Leader Joann Ariola.

Ostreicher believes that events like these can soften political figures and make them more relatable. “It softens him, makes him human in a different way,” she said of Governor Cuomo. “That’s really the goal—humanizing the people we usually only see behind a podium.”

Spotlighting Local Designers and Social Impact

The project also highlights the importance of local designers and social impact. Every official is paired with a creator from their own community, emphasizing New York’s fashion economy. Last year, Inspector General Lucy Lang walked in a look designed by a formerly incarcerated tailor—an idea Ostreicher pushed for despite logistical challenges.

This year, the partnership deepens with the show’s nonprofit beneficiary being 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.

Building Relationships and Trust

Ostreicher’s ability to persuade politicians to participate in the event stems from years of relationship-building. She started her career in politics after an unexpected pivot from pre-med studies. Inspired by a lecture from Bill Clinton, she shifted her focus to health policy. She earned two master’s degrees before working on campaigns, including a stint as regional director on Mike Bloomberg’s 2020 presidential bid.

During the pandemic, she turned to Zoom and launched a video interview series with local leaders. Over time, she built a reputation as a friendly and accessible media personality who could draw politicians out of their talking points. Her show, Political Personalities with Skye, became a platform for connecting viewers with legislators, showcasing their personal lives and interests.

When Ostreicher calls with another “wacky idea,” officials trust her. “They know it’s going to make them look good,” she said. This trust has led to strong support from sponsors, including Airbnb, Uber, EmblemHealth, Aeon Nexus Corporation, and local partners like Beauty Social Salon and Rethink Food.

Expanding Beyond New York

Ostreicher’s long-term vision extends 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 she reflects on her journey—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.