Harry Styles became an official ambassador for Gucci in 2018, starting with an advertising campaign that made him the face of Gucci Tailoring, featuring short videos and photo campaigns showcasing various tailored suits.

Harry Styles launched Pleasing in late 2021, serving as the founder and creative director. He oversees product development and has collaborated with designers like Marco Ribeiro, while also featuring rock legend Mick Fleetwood as the new face of the brand, blending their cross-generational friendship in the beauty industry.

Harry Styles has taken a minority stake in S.S. Daley, supporting the emerging British label's growth and longevity as announced after designer Steven Stokey-Daley’s show at Pitti Uomo.