The most important role of footwear is to ensure safe, functional walking, and foot protection. For the proper functionality of not only the work shoes, the anti-slip behavior of the shoe under various conditions and environments plays an important role in the prevention of slips, trips, falls, and consequent injuries. This article is intended to review the current understanding of the frictional mechanisms between shoe outsoles and various counterfaces that impact the evaluation of outsole slipperiness. Current research focuses on the mechanisms driving outsole friction on different ground surfaces or the definition and description of parameters that influence outsole friction. Subsequently, the review discusses the effect of various surface contaminants on footwear friction. Lastly, challenges and outlooks in the field of footwear outsoles are briefly mentioned.