The contrast mechanism in Kerr imaging is the apparent angle through which the plane of polarization is rotated upon reflection from a magnetic surface. This can be calculated for a well characterized surface given the polarization state of the incident light. As in traditional optical microscopy, the spatial resolution is limited by diffraction to roughly half the wavelength of the illumination light. The diffraction limit can be circumvented through the use of near-field scanning optical microscopy, in which the illumination source is an evanescent field at the tip of a tapered optical fiber. A novel probe design for near-field optical imaging in reflection mode will be proposed, and experimental work on the development of a near-field Kerr microscope performed up to this point will be presented. The complication in merging these two techniques arises from the complex polarization profile of the evanescent field. This profile can be characterized for a given probe geometry with the use of electromagnetic field modeling software, allowing for subsequent modeling of the polarization profile of the optical response. An algorithm for predicting the optical response to a near-field probe tip from a generalized multilayer thin-film is presented.