In this paper an innovative approach to microwave imaging, which combines a qualitative imaging technique and deep learning, is presented. The goal is to develop a tool for reliable and user-independent retrieval of the shape of unknown targets from the knowledge of the scattered fields. Qualitative imaging methods are powerful inverse scattering tools, as they provide morphological information in real-time. However, their outcome is a continuous map which has to be hard-thresholded to clearly identify the targets. This thresholding unavoidably results in case-dependent, often user-biased, results. To deal with this issue, a deep learning approach, based on a physics-assisted deep neural network is proposed to automatically classify image pixels, i.e., to generate binary masks, separating the targets (foreground) from the background. In particular, the proposed network binarizes the output of a qualitative imaging inversion technique known as orthogonality sampling method. For the sake of comparison, a deep learning method is also exploited, which generates the binary masks directly from the scattered fields without any qualitative imaging aid. A quantitative assessment of the performances of both methods as well as a test on experimental data are provided.