By: Damilola Bankole

The Columbia University Fashion Society was delighted to host Dylan Kelly for an intimate conversation, where members gathered for a glimpse into his mindset, career journey, and creative philosophy. Since launching his now-iconic “Walk With Me” series, Kelly has featured figures like Alex Consani, Bhavitha Mandava, and Honey Balenciaga on his pages, earning nods from A$AP Rocky and The New York Times. The same charismatic energy that animates his videos entered the room before he even finished his first sentence.

When asked about the origins of his work ethic and love of fashion, Kelly traces it back to an early interest in writing and personal style – although he admitted it took time to find the right environment to cultivate it. He began to explore these interests more seriously at Tufts University, where the environment felt far more open-minded than what he had been used to in the past. Eventually, he transferred to the Fashion Institute of Technology in Manhattan, placing him squarely in the orbit of the industry that he had been studying from afar. Once there, he wasted no time interning at L’Officiel USA, V Magazine, and Paper Magazine while studying advertising and marketing communications. 

Kelly described his early career in the most refreshing candor. His first internship at L’Official was, quite perfectly, a result of a direct message on Instagram. One connection led to another, and soon he was building a network across publications. The lesson, he noted, was simple but often ignored: talk to people, stay curious, and don’t be afraid to move on from something that does not feel right. After graduating, he joined HYPEBEAST as an Associate Editor and rose to Senior Editor in just four years!

It was during his time at HYPEBEAST that Kelly, along with his close friend and manager Hailey Long, developed the concept for “Walk With Me”. The series’ format is now instantly recognizable: a quick question, a cheeky response, and then the iconic invitation that we all love to hear. What follows is an engaging, Miranda Priestly-esque lesson in fashion, history, and trends. 

When asked what makes the videos resonate so strongly, Kelly emphasized the importance of carving out a niche. In the digital landscape saturated so heavily with content, imitation is the quickest route to a burning pile of invisibility. His advantage, he explained, was his editorial background. Years in fashion publications trained him to rapidly condense complex ideas into digestible, intelligent commentary. 

The voice of “Walk With Me” is also unmistakable. Kelly has truly leaned into the persona inspired by Miranda Priestlty’s cerulean monologue in The Devil Wears Prada. The result is a deliciously charismatic and instantly recognizable delivery. His own personal style remains front and center, but always in conversation with the larger cultural moment. He referenced DSQUARED2’s winter sport inspired show and Hudson Williams’ distinct runway walk as examples of how designers can stay true to their aesthetic, while still responding to the zeitgeist. And, in true editor fashion, he reminded the room that none of it happens without practice. For example, the first “Walk With Me” took nearly twenty minutes to film!

As his online presence grew, Kelly decided to face the decision to step into the independence of full-time social media. Since then, his audience has expanded rapidly, bringing both the highs and inevitable turbulence of the internet. Still, he noted that the most meaningful feedback comes from young creatives who say his work gave them the confidence to enter the industry. The Columbia Fashion Society can affirm that his advice gave us all the confidence in the world.

Looking ahead, Kelly plans to continue expanding his presence on Instagram and TikTok while exploring new formats and platforms. He recently introduced “Walk With Us,” an extension of the original series that spotlights the stories of influential figures in the fashion industry. Now backstage at New York Fashion Week, we cannot wait to hear his eloquent and fascinating opinions on the new collections. 

The Columbia University Fashion Society extends its sincere thanks to Dylan Kelly and Hailey Long for joining us, and for letting us briefly walk with them.