In this Letter, the design of a directional optical cloaking by a genetic algorithm is proposed and realized experimentally. A three-dimensional finite-difference time-domain method is combined with the genetic optimization approach to generate the cloaking structure to directionally cloak a cylindrical object made of a perfect electrical conductor by suppressing the undesired scattered fields around the object. The optimization algorithm designs the permittivity distribution of the dielectric polylactide material to achieve an optical cloaking effect. Experimental verifications of the designed cloaking structure are performed at microwave frequencies, where the proposed structure is fabricated by 3D printing. The imperfect conformal mapping from a large-scale permittivity distribution and the compensation of the remaining scattering by a small-scale permittivity distribution are the basic physical mechanisms of the proposed optical cloaking.