The shoes, targeted to the junior market, range in price from $40 for the "Venice" canvas flat to $100 for the "Hailey" boot, a combat-like lace-up.
Other styles include "Sofia," a platform heel with ruffle T-strap for $60, "Lara," a studded sandal for $50 and "Rio," a gladiator-type sandal for $50.
The Sofia ruffle shoe and Hailey combat boots will be available on JCPenney.com and in select stores starting November 6.
The rest of the Olsenboye styles will roll out in February.
"Steve and his team are very excited about the opportunity to join forces with Ashley and Mary-Kate to create aspirational, trend-right fashions at affordable prices," Edward Rosenfeld, Steve Madden's chairman and chief executive officer, said in a release.
Madden is no stranger to JCPenney. His company also manufactures shoes for the chain's Fabulosity line.