“Ripped to Shreds” is a biweekly column by Jaxon Havens about fashion politics.
In the style of a downtown New York City flasher, Andrew Cuomo flipped open his blue suit jacket on the runway and revealed a satin lining stamped with iconic images like Marilyn Monroe’s face. The suit was designed by Gina Newman of Bond and Bari, a local woman-owned business, to be showcased at the 2025 “Style Across the Aisle” event. Held on September 10 at New York’s Surrogate’s Court, the event was sponsored by UBER, who plastered their logo across panels lining the runway. The first iteration of the event was held one year prior, founded by media personality, Skye Ostreicher. This year’s fashion show raised funds for Witness to Mass Incarceration, a non-profit that helps the formerly incarcerated. “Style Across the Aisle” claims to use fashion to bring New Yorkers together across the political divide and to humanize the people who work in politics. Yet, can the fun of fashion really obscure the political nature of the event? And what good comes from this kind of “humanization” of already-human politicians? When does it turn more into trying to give a facelift to a tainted political career?
At the inaugural “Style Across the Aisle” event, Ostreicher emphasized a desire for fashion to “neutralize a hot topic like politics” and humanize elected leaders, while also giving them a chance to “recognize local small business owners from their districts.” The event’s intention is not apolitical, but anti-political, attempting to isolate politicians in a vacuum of innocence. Using politicians while claiming to neutralize politics creates an uncomfortable dissonance—a non-political fashion show would be most effective by not including politicians at all. The participating politicians, as well as the discourse which emerges from the event’s existence, are not immune from critique.
Of the very few Republicans making their presence known at the event, current Republican mayoral candidate Curtis Sliwa stood out in his signature red beret. The overwhelming presence of Democrats at a purportedly “bipartisan” event is expected for New York politics. Yet, it should serve as a reminder that the people making such grand appearances are, or formerly were, working jobs that make up the face of the city. They are the chosen few who show off local designers’ work at this kind of elite event. Yet, as a gathering, the show is quite enigmatic, raising questions of “why” and “how” it came about.
Skye Ostreicher’s family ties gave her an early glimpse into politics—her great-uncle, Queens congressman Benjamin S. Rosenthal, was eulogized by Mario Cuomo in 1983. Though her father is an orthodontist and she does not come from any political dynasty, she grew up aware of politics’ personal side. Ostreicher frames her work around distinguishing “good” from “bad” politicians through their human character, arguing that too much focus falls on political party membership. Her method of “good/bad” character assessment is so foolproof that she allowed sexual predator Andrew Cuomo to walk in the show. Ostreicher even embraces her own lack of a critical perspective, telling Morning Honey, “I never ask hardball questions.” Instead, relishing in the fluffy joy of rubbing elbows with powerful people, Ostreicher seems to skirt around the meat-and-potatoes of the political world altogether.
Ostreicher wore an “I Love Cuomo” T-shirt in 2024, writing on Facebook that she has owned it since 2020, one year prior to his resignation. Ostreicher’s Instagram handle is, after all, @thepoliticalpersonality. She makes politics the motif by which she brands her own personality, so it is only natural that she has her own agenda. With that in mind, what is the public to understand from the 2025 “Style Across the Aisle” show if not a poorly-disguised endorsement of Cuomo? Four years after Cuomo’s resignation, Ostreicher is still wearing the T-shirt. Cuomo gets to show up to strut down the runway, in full glam, and fraternize with Sliwa and former colleagues. Further, the whole event is put on by a young media worker with a distant family-friend connection to Cuomo. Call it networking or call it serendipity, the event is a honey pot of good press for Cuomo, which he desperately needs after losing the 2025 New York City Democratic mayoral primary to Zohran Mamdani. Yet, if his goal is truly to be “humanized,” as per the crux of Ostreicher’s many ventures, the event is ultimately a failure. Walking down a fashion runway in an expensive suit doesn’t make him any more relatably “human,” and it’s unlikely he endeared himself to any newfound-supporters.
Cuomo has the privilege of enjoying the aesthetic games of an “apolitical” fashion show and uses it as an easy way to boost his image without being judged on his character or policy. It is all for charity, of course, so how could one critique him? Cuomo emphasized the event as being “a great bipartisan effort and a reminder, there’s far less that divides us than unites as New Yorkers.” Perhaps Cuomo is trying to curry favor with Republicans who see him as a more formidable opponent to Mamdani than the Republican candidate, Sliwa. Or perhaps his statement is just an empty sack of words to throw out after having a fun night with his rich friends.
Ostreicher’s approach, overall, is not without merit, and the ambition behind a humanization of the worlds’ politicians is warmly empathetic in a world with too-little empathy. Certainly some good comes from the event, raising over $75,000 for a good cause. It is, however, ironic that Ostreicher has chosen Witness to Mass Incarceration as the charity of the year, when she had formerly worked as the regional director of the 2020 presidential campaign of Mike Bloomberg, who famously expanded the “stop-and-frisk” policing in NYC, which undeniably contributed to the disproportionate incarceration of marginalized communities.
Ostreicher is also correct that politicians are human. Cuomo—human as ever—resigned from his mayoral position due to a sexual harassment scandal—a stain on his résumé he will live with forever. He is human, but he is a human who has caused irreparable harm to others—not only to the women who he allegedly harassed. Cuomo also mandated that elderly COVID-19 patients from nursing homes be quarantined in said homes, which led to an outbreak amongst some of the city’s most vulnerable. Cuomo then lagged on releasing data about COVID casualties, and he ultimately spat out a “Who cares?” when questioned about the people who had died. His politics are not only publically damaging, but deeply personal because the people affected by his actions and his policies have been impacted in deeply personal ways.
You don’t have to be a sex criminal or the Boogeyman to be entangled in deeply personal politics. But a political context is constantly underlying our personal experiences, so it’s misguided to put aside politics for the purposes of illuminating someone’s humanity. These placid bodies, walking down a strip of UBER-branded panels, hope to lull the public into a dreamy ignorance as the audience “oohs” and “ahhs” at a night of show and spectacle. After the garments are taken off and the night has come to an end, the powerful actors who walked the runway will return to their jobs and continue making choices with real-world consequences. There is nothing extra “human” being showcased just because they got to have a night of fun for everyone to see.
“Style Across the Aisle” aims to humanize politicians and bridge the party gap through fun! And pretty clothes! But it stands as a distraction from a less overt political endorsement of Cuomo. It does not effectively make politicians any more relatable to ordinary people. The event is founded on ideologies that fundamentally mischaracterize what it means to need “humanization,” and what it means to be “human.” There is no way to “neutralize” the “hot topic” of politics without ignoring and erasing the lives of regular people impacted by political actions.
If putting politics aside is necessary to humanize politicians, perhaps the issue is the anti-human nature of their politics.
