Roy Fleeman is the Vice President of Design at Vacation®, where he leads the brand’s award-winning visual identity, creative direction, and packaging design. With a deep love for the nostalgic aesthetics of his 90s childhood, Roy has helped shape Vacation® into a modern lifestyle brand that blends high design with playful escapism.

At Vacation®, Roy oversees everything visual from packaging and creative campaigns to retail graphics and fixtures, building a cohesive world that feels both nostalgic and relevant. His approach fuses elevated art direction with “a little bit of undesigned charm” — a timeless sensibility inspired by the simpler, less-digitized aesthetics of the late twentieth century.

Before joining Vacation®, Roy led a small agency branding and packaging for clients including Sony Music, Patagonia, the City of Atlanta, and multiple hospitality clients across the globe.