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Ruby followed in her mother's footsteps by becoming a high fashion model. She signed to Nous Model Management in Los Angeles and Select Model Management in London. Her older half-sister Kimberly Stewart is also a model. Ruby did runways for Karen Walker for her Spring/Summer 2006 collection for London Fashion Week during 2005. Walker praised her "unpretentious youthfulness".
In the summer of 2010, Ruby formed the Los Angeles based band, Revoltaire, along with Jason Yates (guitar,keys) and Chris Cano (drums). The band completed an album's worth of material titled “Painted Hour Glass", with Ruby as the vocalist and lyricist. In 2012, Revoltaire disbanded.