Walk With Us: Dylan Kelly on NYFW

Is New York Fashion Week dead? Designers decamping to Paris. Editors whispering of early departures before the last look even clears the runway. The NYFW eulogy has become an industry reflex, putting real pressure on its designers for years.

How can this be true? It’s New York Fashion Week. Let’s talk about it.

Amid the noise, Dylan Kelly offered OhSoAnnie something far more useful than another obituary. Thanks to the “Walk With Me” genius himself, we get a walk-through of the week as it actually felt on the ground. By now, he’s everywhere that matters. Backstage before the first look, front row before the lights dim. Phone up, story posted, while everyone else is still looking for their seat assignments. In a fashion week saturated with commentary, Dylan has become one of the most important voices actually worth listening to.

So when he said this season felt different, I paid attention.

“What felt different about the energy of New York Fashion Week this season?”

“There’s a heightened pressure for New York to be good,” Dylan told me. The narrative that NYFW is losing its momentum hasn’t exactly disappeared, and he was refreshingly honest about it. “NYFW is not dead,” he said, but undoing that stigma is another matter entirely.

Still, this season felt like a real effort to push forward. He pointed to Rachel Scott’s debut at Proenza Schouler as a symbolic start of a new era, looking to the future rather than relying solely on nostalgia. “It was a juxtaposition,” he explained. An “experimental designer stepping into a legacy house and giving it new meaning.” 

At Bronx and Banco, models stepped out of taxi cabs in a perfectly theatrical tribute to the city. As Dylan put it, “It felt like the city itself had wandered onto the runway.” The style has always been here, he noted, but to keep the city itself at the forefront, “you have to find the New York moments." 

“Which emerging designers are you rooting for right now?”

Dylan has always had an instinct for spotting talent early, and two names surfaced repeatedly.

First, Kieth Herron of Advisry. “New York is home, and you can feel it,” he said. The collection featured motifs and utilitarian jackets with functional pockets – pieces that reflect how people actually move through the city  

Pipenco Lorena, meanwhile, stood out for the opposite reason. Kelly described her show as tapping into “full fantasy,” complete with larger-than-life hats and dramatic silhouettes. What makes her work compelling is the balance. Beneath the performance are real, enticing pieces. “Editorial and commercial are hard to balance,” he noted.

As someone who shares her Romanian roots, I have been rooting for Lorena as well. There is something especially thrilling about watching a designer from our corner of the world step onto the New York City stage with this much imagination.  

“Which show best captured the spirit of New York right now?”

“Coach always gets New York,” Dylan said, without hesitation.

At the classic Cipriani Downtown venue, guests arrived through a line of taxis, carrying apple-shaped bags and Statue of Liberty charms dangling from their belts. It was playful, almost literal, and completely authentic to the city. 

For Dylan, Coach’s Stuart Vevers understands the crucial need to design something for the new generation of New Yorkers without losing the brand’s heritage. The room was filled with real, New York people that made it feel like home.

“What’s happening backstage that would surprise people?”

“Everything moves really fast,” Dylan said.

Backstage, he was struck by the sheer “breadth of talent” packed into those crowded rooms. One of his favorite moments was watching Pat McGrath work on Queen Alex Consani’s face. No livestream or TikTok recap can quite capture the mastery at work. So much of the magic of fashion week is happening backstage. Thanks to Dylan, we got a little sneak peak!

Adding to the week’s list of surreal encounters was Dylan’s interview with Martha Stuart for Carolina Herrera’s Good Girl fragrance campaign. He described the exchange as “unintentionally hilarious,” as Steward — arguably the most put-together woman alive — earnestly explained on camera why she qualifies as a “good girl”.

Through all the bustle and glamour, he said, the environment is "surprisingly warm.” Busy, yes. But people are happy to talk, share stories, and be part of it all. 

“If someone could only attend one show this season, where would you send them?”

“Easily, Veronica Leoni at Calvin Klein.” 

He described it as a true fashion show. No distractions, no gimmicks, no oversized set pieces. Clean, sophisticated, sharp tailoring, with perfect lighting and clothes that held their own in real life.

The room itself was part of Leoni’s statement. The front row was dressed almost entirely in Calvin, turning themselves into a genius advertisement of the collection. The lighting was ultra-crisp and ideal for examining every cut and proportion before them. As the master content creator Dylan Kelly puts it, the lighting was "conducive for the both the line and my content.”

Most importantly, “the clothes were simply better.” The cuts were sharper, the silhouettes more confident, the whole collection operating on a level that felt "noticeably above much of the week’s competition”. Calvin Klein stood out for focusing on the clothes themselves. Sometimes, that is the boldest move of all. 

New York Fashion Week, as Dylan made clear, isn’t pretending everything is perfect. However, it is trying so visibly to move forward. Maybe that is the real spirit of the city. The city has never relied on perfection, but always survives on momentum.

So thank you Dylan Kelly for letting OhSoAnnie walk a few blocks of the week alongside you. Your influence is truly changing the industry. I, for one, am already waiting for the next “Walk With Me”.

Xoxo,

Annie