We study the ultraviolet to infrared evolution and nonperturbative behavior of a simple set of asymptotically free chiral gauge theories with an SU(N ) gauge group and an anomaly-free set of nS k copies of chiral fermions transforming as the symmetric rank-k tensor representation, S k , and nĀ ℓ copies of fermions transforming according to the conjugate antisymmetric rank-ℓ tensor representation,Ā ℓ , of this group with k, ℓ ≥ 2. As part of our study, we prove a general theorem guaranteeing that a low-energy effective theory resulting from the dynamical breaking of an anomalyfree chiral gauge theory is also anomaly-free. We analyze the theories with k = ℓ = 2 in detail and show that there are only a finite number of these. Depending on the specific theory, the ultraviolet to infrared evolution may lead to a non-Abelian Coulomb phase, or may involve confinement with massless composite fermions, or fermion condensation with dynamical gauge and global symmetry breaking. We show that S kĀk chiral gauge theories with k ≥ 3 are not asymptotically free. We also analyze theories with fermions in S k andĀ ℓ representations of SU(N ) with k = ℓ and k, ℓ ≥ 2.