Abstract: A footwear assembly structured to be worn on a user's foot is presented. In particular, the footwear assembly comprises an upper engaging component which is cooperatively structured and disposed to secure to the user's foot during use. In addition, the footwear assembly comprises at least one cooperatively structured insole, midsole and outsole. The insole(s) are disposed in an overlying relation to a top surface of an upper portion of the midsole, and the outsole is disposed in an underlying relation to at least a portion of the midsole. In addition, the footwear assembly comprises at least one insert disposed between the midsole and the outsole, for example, proximate a front and/or rear portion thereof, and is structured to provide added support and cushioning. Further, an undersurface of the outsole is structured to define an at least partially arcuate contour along its longitudinal length to facilitate a rocking movement during use.