In this paper, a numerical study is conducted to provide guidelines towards designing a wearable microwave tomography (MWT) system for medical imaging. The main objective is to ease the process of imaging human organs as well as improve the overall image reconstruction of the utilized inversion algorithm. In comparison to conventional MWT systems currently available, a wearable system uses structural information about the object-of-interest (OI) with ease in its design. The information is used to relocate the antennas and the inversion algorithm image domain. In addition, a wearable system uses ultrasound gel as a coupling medium, which is an alternative to a liquid matching medium. As an example, the proposed guidelines are applied on the use of MWT for imaging human lower limbs. The initial results of a simulated wearable system show a better estimation of the relative complex permittivity of different tissues within a OI in comparison to a conventional MWT system.