Designer and Stylist June Ambrose on 50 Years of Hip-Hop

June Ambrose wears many hats — literally and figuratively. The costume designer and creative director has been photographed wearing all kinds of bespoke hats of the years, and she even told the Cut back in 2016 that she owns close to 100 of them. She often posts Instagram photos showcasing her collection, which consists of cartoonlike ball caps, top hats, wide-brim bowlers, chapeaus, and lids with bunny ears by New York–based designer Khia Tullae. It’s her signature look. And aside from being so on the nose — Ambrose wears many professional hats as well, with a long list of accolades ranging from stylist and designer for high-profile clients like Sean “Diddy” Combs, Jay-Z, and Missy Elliott to published author, entrepreneur, television personality, and, most recently, creative director of Puma — her personal style is a testament to her boundless creativity and fearless approach to fashion.

In the mid-’90s, Ambrose made a name for herself in the hip-hop world by becoming an image architect for artists like Jay-Z and Elliott. She not only designed and styled their looks, but she also helped shape their public persona. As the woman behind some of the genre’s most impactful and unexpected style moments, her contributions to hip-hop culture and fashion at large cannot be defined by a single title — she told the Cut that she never wants to “boxed in” as just one thing (i.e., celebrity stylist). Instead, Ambrose’s influence stems from the fact that she was always a few steps ahead of the curve. When fashion houses wouldn’t lend to her clients, she honed in on her costume-design skills and made the looks herself. When the majority of female chart-toppers had an overtly…