Despite their potential benefits, exoskeletons’ acceptance in the workplace is negatively affected by workers’ discomfort caused by poorly fitted devices. Several approaches have been proposed to achieve a better fit through biomechanical analysis or utilisation of body modelling at the exoskeleton design stages. However, direct, real-time user support when putting on an exoskeleton has not been achieved so far. Our research addresses this challenge by providing exergame-like augmented reality (AR) feedback to guide workers in the fitting processes of a passive upper limb exoskeleton. To assess the usefulness and ease of use with regard to our approach, we carried out a feasibility study with twelve participants exploring the potential of AR feedback positively influencing the exoskeleton’s fitting. Consequently, we observed the participant’s preference towards the AR system over PDF instructions, hinting at higher user acceptability than classical methods. Thus suggesting the potential for industrial deployment.