Born  in Seattle, Washington, she is an American artist and designer best known for her eclectic crochet hats and her large scale crochet pieces and mandalas, consisting of colorful concentric circles and repeating patterns. Her pieces are often connected to her ongoing project "Paradise Under Reconstruction in the Aesthetic of Funk".

Her designs are influenced by African, Chinese, and Native American and Eastern philosophies, with undertones of the 1970s "Funk" aesthetic. Her hats have been featured in United Colors of Benetton ads, on The Cosby Show, and in the Spike Lee film Do The Right Thing (worn bySamuel L. Jackson as DJ Mister Señor Love Daddy). In 2003, her designs were commemorated in the form of an Absolut Vodka Ad entitled "Absolut Bailey." Bailey has been artist-in-residence at the Studio Museum in Harlem, the Society for Contemporary Craft in Pittsburgh, and the Marie Walsh Sharpe Art Foundation in New York City. Her work has been exhibited at the Studio Museum of Harlem, the Jersey City Museum, the New Museum of Contemporary Art, and the High Museum of Art in Atlanta. Her work is in the permanent collections at Harlem's Schomburg Center for Research in Black Culture, the Allentown Art Museum, and the Museum of Contemporary Arts and in the Museum of Arts and Design. Some of her crochet work was transformed into mosaics for the New York City Subway's 34th Street – Hudson Yards station.

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