Ask Kyle Hoto Reid to describe his style, and he responds with his mantra: “It’s classy with a hint of ‘Fuck you.’ ” That perfectly crafted sound bite is representative of Reid’s overall approach to life. The fashion-world Renaissance man is supremely gifted at finessing street swagger with consummate professionalism, a skill he demonstrated first at Dream Design (the lifestyle retail boutique he ran until 2009) and, more recently, in his collaboration with the hat company Brimz. “My eye is attracted to clean spaces and minimalist style with a touch of something that doesn’t belong—a paint spot here or a rip there,” Reid explains. His appreciation of the unexpected extends to his work building brands for individual clients like America’s Next Top Model icon Chantelle Winnie, whose Instagram features shots of her in offbeat locales like helipads and amusement parks. Says Reid, “I don’t like it when things are too perfect.”
Jamie Webster’s job is to make things look cool—whether it’s a car commercial or a music video for Majid Jordan, the pop duo signed to Drake’s record label