The Style of Legacy: Celebrating Charles Gregory’s Bold Impact in Fashion, Tech, and Culture

There’s a rare kind of magic that happens when two artists grow side by side for over two decades—challenging each other, creating together, and most importantly, supporting each other through every elevation. That’s the magic I’ve experienced as both an artist and a friend with the legendary Celebrity Stylist Charles Gregory. Over the years, I’ve had the honor of working with him, being advised by him, and standing witness to a creative force whose influence stretches far beyond the runway.

Charles Gregory isn’t just a stylist—he’s a cultural architect. His recent ventures have been nothing short of groundbreaking, bridging the worlds of AI, tech, and fashion in ways the industry has never seen. Just last night, during the 2025 Met Gala, he hosted an exclusive Met Gala Watch Party that not only celebrated high fashion but spotlighted the future of fashion through the lens of innovation. Charles continues to push the culture forward—never behind.

Charles Gregory alongside Nina Capone 2025 Met Gala Watch Party

@the_glamazonrema

But his magic doesn’t stop at couture. A few years ago, Charles curated a tech-infused fashion show for the Nicetown Giveback 25th Anniversary celebration. That show wasn’t just about clothes—it was a story of community, evolution, and excellence. Using augmented reality and smart fabrics, he created a visual experience that honored the past while opening doors to the future. The Nicetown event proved once again why his name carries so much weight in both fashion and community circles.

Like myself, Charles Gregory isn’t confined to one lane. While I rock mics and engineer podcasts with my tech brain and hip hop heart, he’s out here using his voice and vision as a co-host on “We Talk Weekly,” delivering compelling conversations that resonate with fashion lovers, creatives, and forward-thinkers alike. His presence on that platform reflects his versatility, his intellect, and his passion for storytelling. Trust me—when Charles speaks, the room listens.

Our 20+ year friendship has been dynamic, filled with encouragement sessions, suggested looks, creative brainstorms, runway shows, interviews, and real-life growth. As a podcasting techie and hip hop artist, I know how hard it is to wear multiple hats and keep your integrity intact. Charles Gregory wears them all—fedora, crown, and thinking cap—without ever compromising his authenticity.

He is, without a doubt, one of the most inspiring figures in fashion and culture today. And as he continues to shape the future through AI, innovation, and style, I’m proud to not only call him a collaborator—but a brother.

Stay tapped in, because Charles Gregory isn’t just making fashion history—he’s rewriting it.

— Nina Capone Hip Hop Artist | Tech Visionary | Podcast Host Inspire Da Streets Radio