Stylist Jenna Tyson Elevates Hip Hop Fashion with Pucci Princess Dressing

Stylist Jenna Tyson shares her fashion journey with EBONY, reflecting on the influences that shaped her career. “My grandfather was really into proper dressing. He’d crease his pants from top to bottom and had a fire suit game,” Tyson reminisces. Her grandfather’s “exotic cowboy boots” and “buckles” outings ingrained the artistry of a strong wardrobe in her. “Part of our relationship was him taking me shopping, so dressing well became a prideful part of who I am,” she says.

Despite her early exposure to fashion, Tyson initially aimed for a medical career. “I really wanted to go to med school and become a plastic surgeon,” she says. However, her knack for fashion became apparent through retail jobs. “The summer I graduated from high school, I worked at a local clothing store in Orange County. My boss asked, ‘Why are you going to school for medicine when you love fashion?'” That question sparked a realization and a new career path.

Tyson moved to New York and attended FIT, focusing on millinery. She worked retail jobs to support herself while drawing inspiration from stylist Mariel Haenn, who was transforming Rihanna’s style. “Haenn turned Rihanna into a rock star, an aesthetic rare for Black women at that time,” Tyson notes. Researching Haenn led Tyson to stylist Misa Hylton’s legacy. “Learning about Hylton’s journey made me realize I needed her as a mentor.”

Tyson joined Hylton’s fashion academy’s inaugural class in 2012. “Hylton got me consistent internships, and I was doing festival runs in Brazil and Abu Dhabi,” she says. Despite the glamor, Tyson emphasizes the hard work behind the scenes. “It was tough but impactful work. As an assistant, I organized hangers, shoes, and clothing,” she recalls, crediting stylist Tiffany Hasbourne for invaluable early lessons.

Hylton’s advice led Tyson to hip-hop styling, a decision that changed her career trajectory. “She suggested hip-hop styling for a well-rounded experience,” Tyson explains. Now, Tyson is the personal stylist for Flo Milli, integrating Pucci’s vibrant prints into her wardrobe. “We connected with Pucci in Milan, and it was just synergy,” Tyson says.

Tyson’s work with Flo Milli mirrors Haenn’s and Hylton’s iconic styling. “Like Misa with Kim, there’s something sexy and raw in blending ghetto and high fashion,” Tyson says. She aims for bold, show-stopping looks. “I’m all for quiet luxury, but sometimes you need to be loud.”

With over a decade in the industry, Tyson’s momentum continues to build. She offers advice to aspiring stylists: “Enjoy all the moments on your journey, appreciate them, and celebrate every forward motion as a success.”

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