This book deals with nonsmooth structures arising within the optimization setting. It considers four optimization problems, namely, mathematical programs with complementarity constraints, general semi-infinite programming problems, mathematical programs with vanishing constraints and bilevel optimization. The author uses the topological approach and topological invariants of corresponding feasible sets are investigated. Moreover, the critical point theory in the sense of Morse is presented and parametric and stability issues are considered. The material progresses systematically and establishes a comprehensive theory for a rather broad class of optimization problems tailored to their particular type of nonsmoothness.