A wideband wearable electromagnetic (EM) head imaging system for brain stroke detection is presented. The proposed system aims at overcoming the challenges of size, rigidity, and complex structures of existing systems. The proposed system is built into a light-weight and compact imaging platform, which integrates a 16-element antenna array into a highly flexible custom-made wearable cap made of a cost-effective and robust room-temperature-vulcanizing (RTV) silicone. The system mitigates the mismatch between the skin and antenna array by introducing a flexible high-permittivity matching layer. The utilized compact antenna demonstrates wideband operational frequency over 0.6-2.5 GHz with a low signal distortion, safe values of SAR, and unidirectional radiations. The system is experimentally validated on realistic head phantoms. The polar sensitivity encoding (PSE) image processing algorithm is utilized to generate 2D images of different testing scenarios. The obtained images of a stroke-like target inside the head phantoms demonstrate the merits and feasibility of the system for preclinical trials.