Diabetes is highly prevalent throughout the world and imposes a high economic cost on countries at all income levels. Foot ulceration is one devastating consequence of diabetes, which can lead to amputation and mortality. Clinical assessment of diabetic foot ulcer (DFU) is currently subjective and limited, impeding effective diagnosis, treatment and prevention. Studies have shown that pressure and shear stress at the plantar surface of the foot plays an important role in the development of DFUs. Quantification of these could provide an improved means of assessment of the risk of developing DFUs. However, commerciallyavailable sensing technology can only measure plantar pressures, neglecting shear stresses and thus limiting their clinical utility. Research into new sensor systems which can measure both plantar pressure and shear stresses are thus critical. Our aim in this paper is to provide the reader with an overview of recent advances in plantar pressure and stress sensing and offer insights into future needs in this critical area of healthcare. Firstly, we use current clinical understanding as the basis to define requirements for wearable sensor systems capable of assessing DFU. Secondly, we review the fundamental sensing technologies employed in this field and investigate the capabilities of the resultant wearable systems, including both commercial and research-grade equipment. Finally, we discuss research trends, ongoing challenges and future opportunities for improved sensing technologies to monitor plantar loading in the diabetic foot.