When music and fashion meet: Reflections from Jazz Meets Hip Hop

As a fashion designer music has always played a significant role in my creative process. Many of my collections have been inspired by the music I was listening to at the time. A song creates a feeling, a mood or an emotion that eventually finds its way into fabric, colour and silhouette. That is why I was particularly excited to attend the Jazz Meets Hip Hop: A Black Music Month Conversation, held at Toronto’s Pilot Tavern as part of the Toronto Jazz Festival.

The event brought together artists, musicians, and industry professionals to discuss the evolving relationship between jazz, hip hop, and contemporary music. What really caught my attention was the discussion on how easily we can discover new music and trends today. Unlike previous generations, who often had to search through record stores and make a deliberate effort to find new artists, today’s listeners are guided by algorithms. A jazz song can appear immediately after a hip hop track, introducing audiences to music they may never have actively sought out on their own.

As someone who writes about fashion, I was equally interested in the visual identity of the artists on stage. Canadian Jamaican recording artist Kreesha Turner embodied a look that felt effortlessly modern. Dressed in a fitted grey jumpsuit layered under a black bomber jacket and paired with sneakers, she projected a sense of comfort and authenticity. Her signature curls were swept up high, framing her face and reinforcing the relaxed, approachable aesthetic she has embraced during this latest chapter of her musical journey. I was curious to learn how the music she creates influences the way she dresses. Kreesha explained how her personal style has evolved alongside her career. “I’ve lived through different eras of myself. In my pop days, everything was extremely focused on high fashion and current trends. Then, when I moved into reggae, the cultural influence of Jamaica had its own impact on my fashion. Now, in the jazz space, I wanted to simplify things.”

Her latest album explores healing, reflection, and self-discovery after heartbreak, and that theme extends into her wardrobe choices. “For me, in this era of my life, doing jazz, it’s definitely more of a cozy attire. I want listeners to feel like I am at home relaxing, drinking a cup of tea. This project is specifically about the process after a breakup, when you are sitting with yourself, reflecting, sipping your morning tea, processing why you did the things you did, and why your partner or ex-partner did the things they did.”

I had that exact feeling when Kreesha first walked onto the stage. Her cozy look, mixed with a touch of sexiness and effortless cool-girl energy, made me want to admire her beauty while listening to her soothing voice. When asked about her fashion influences over the years, she mentioned Kylie Minogue as an early inspiration and credited Rihanna as having a significant impact, particularly because of her Caribbean roots. Today, however, she is focused on creating her own visual language.

The members of The Soul Rebels brought a different energy to the stage. Dressed in black and wearing graphic T-shirts featuring legendary hip hop artists, their style reflected the fusion of jazz tradition and hip-hop culture. Despite arriving in Toronto after a late-night performance in Buffalo, they delivered an energetic live set that captivated the audience and highlighted exactly why the group’s genre-blending sound has earned international acclaim.

The event served as a reminder that music is not only heard, it is also seen. Through fashion, artists communicate identity, emotion, and intention before a single note is played. Whether through jazz, hip hop, reggae or pop, style remains an essential part of the story artists tell the world.