In 1982, Reebok introduced the Reebok "Freestyle", a woman’s athletic shoe designed for aerobic exercise. This new shoe marked a shift in the athletic shoes market towards athletic shoes designed for sports other than jogging (aerobics, basketball, etc.) and towards the female market for sports shoes (before the 1980’s jogging was primarily a "man’s" hobby). With a price tag of 60 dollars, the Reebok was shockingly expensive at the time. Some people called it the most expensive sports shoe in the world.

The original Freestyle was an Oxford-style (lace-up) shoe made out of white leather. It was adorned simply with the word "Reebok" in light blue lettering and a picture of the British Union Jack flag on the side of the shoe. The original Freestyle was a low top with a yellow gum sole. In the mid 1980’s Reebok released the distinctive high-top Freestyles. In addition to laces, these shoes closed with two Velcro straps around the ankle. They were available in bright, funky colors such as pink, orange, green and yellow. Most of the high-top Reeboks were made out of leather but some canvas and mesh versions of the shoe were also released on the market.

Reeboks were a hit among the new female athletic market. The shoe sponsored the Los Angeles Lakers Girls in the 1980s, and the shoes soon became a hit with cheerleading squads and dance teams across the nation. In addition to athletics, the Freestyle quickly became something of a fashion must-have. Cybill Shepherd complemented her black strapless gown with a bright orange pair of Freestyles at the 1985 Emmy’s. Punky Brewster started the trend of wearing two different colors of Freestyle (an orange on the left foot and a purple on the right foot, for example) at the same time.

On the 25th anniversary of the release of the Freestyle, Reebok decided to launch a campaign it called "Freestyles Forever". This campaign selected six celebrity women (actors, singers, models, etc.) from six major cities in the world. Ali Yasuda, the first Japanese NFL cheerleader, represented Tokyo; Nikki Beatnik, a popular British DJ, represented London; Yelle, the French singer, represented Paris; Sagarika Chatghe, a Bollywood star from India, represented New Dehli; Bimba Bose, a internationally acclaimed model from Spain, represented Madrid; and actress Sheetal Sheth was the face of Freestyle for New York. The event was designed to look back and celebrate the culturally pertinent history of the Reebok Freestyle shoe.