This dissertation provides details regarding the implementation of curved-focal surface fiber coupled imaging for medical and wide-field applications. An optomechanical fluid-filled eye model with visual acuity better than 20/20 vision was design and characterized. A wearable telescopic contact lens was worn on the optomechanical eye model and the performance characterized. Measurements of the contact lens surfaces were modeled to quantify the impact of contact lens fabrication on end-result resolution. Separately, the limitations of the field of view in fiber coupled monocentric imaging are analyzed. This dissertation describes a novel technique to address this based on conformal micro-optics. The design, simulation, and fabrication of an embossed surface relief micro-prism that increases the field of view are demonstrated