Cindy Bear was originally designed by Ed Benedict. One early sketch saw her clad in a bonnet, a frilly scarf and an apron with an elongated, pointed muzzle. A second sketch dropped all accessories save the frill scarf and shortened her muzzle.
Cindy made her debut in the 1961 television series The Yogi Bear Show as a semi-recurring character. Her finalized animation design featured blue/grey fur, a hat, a white frill scarf and a necklace.
Cindy appeared prominently in the 1964 feature film Hey There, It's Yogi Bear in which she is kidnapped, spurring Yogi and Boo-Boo to come to her rescue. She was redesigned by art director Iwao Takamoto for the film into the more familiar modern version with taupe fur, a flower, a light blue skirt and a yellow handkerchief like scarf.
Cindy has received a few slightly different, one-off redesigns. In Yogi's First Christmas, she was given dark brown fur and white hair, as well as a number of different outfits which she wore throughout the film. For the Spümcø short "", she retained her modern character design, but with the blue/grey fur of her original design. featured a preteen Cindy Bear with a significant redesign, wearing a modern 1990s outfit consisting of a white skirt/top, purple jacket, purple shorts, white boots and a ponytail.