Rational design strategies for mechano-responsive optical material systems are created by introducing a simple experimental system that can continuously vary the state of bi-axial stress to induce various wrinkling patterns, including stripes, labyrinths, herringbones, and rarely observed checkerboards, that can dynamically tune the optical properties. In particular, a switching of two orthogonally oriented stripe wrinkle patterns from oxidized polydimethylsiloxane around the critical strain value is reported, as well as the coexistence of these wrinkles forming elusive checkerboard patterns, which are predicted only in previous simulations. These strain-induced wrinkle patterns give rise to dynamic changes in optical transmittance and diffraction patterns. A theoretical description of the observed pattern formation is presented which accounts for the residual stress in the membrane and allows for the fine-tuning of the window of switching of the orthogonal wrinkles. Applications of wrinkle-induced changes in optical properties are demonstrated, including a mechanically responsive instantaneous privacy screen and a transparent sheet that reversibly reveals a message or graphic and dynamically switches the transmittance when stretched and released.