At 16, Dillard-Toone won a full scholarship to the Pratt Institue of Technology and has a degree in fine arts with a concentration in fashion merchandising and marketing. She worked as a fashion illustrator, sewing instructor and a designer before modeling.
Dillard-Toone was the second African American woman to appear on the cover of Vogue (Beverly Johnson was the first "Black" woman on the cover. Donyale Luna never identified herself as "black" so many people stripped her of that honor.) and graced other fashion mags like Essence, Mademoiselle and Cosmopolitan.
Dillard-Toone founded a hair salon, Turning Heads Salon, and has a beauty and holistic living advice article featured in magazines and newspapers around the globe. The model is also an artist. She now owns a physical and online art gallery in New York City with her husband called Indasa Fine Arts Gallery. She and her husband also operate two bed and breakfast hotels in Harlem.