A large number of world population suffer from vision related diseases/defects. Visual health supervision is important for detection, prevention and treatment of eyes disorders. Images of retina/fundus are important for diagnosis of eye diseases. In this paper we report on design and development of a wearable eyeglass type retinal imaging system using a 2D MEMS scanner for ocular health monitoring. Several wearability criteria for instance weight and size factor should be taken into account while designing a wearable health monitoring system. The 2D-MEMS scanner used in the system is small in size, that helps to fabricate an easy to use and lightweight wearable imaging device. The net weight of fabricated system including optical components is 150 g. Sensitivity of the system was estimated by measuring the signal-to-noise ratio for high and low reflectance materials. Signal-to-noise ratio was 7 for high reflectance material and about 4 for biological samples. Imaging results were obtained by scanning a model eye, ham slice and enucleated swine eye in real time by custom made LabVIEW program. The fabricated system has adequate sensitivity and resolution for the observation of retinal arteries and optic disc for detection of eye diseases.