The use of walking aids is widely acknowledged as one of the most relied-on forms of assistive technology. Using stick-shaped devices, such as a cane, is often the entrance for many people to the world of assistive technologies, often accompanied by the negative stigma associated with ageing and disability. This study investigated the perception of disability and needs of the Hong Kong population using walking aids, aiming to inform device design and service provision. We observed 391 individuals using cane-like devices in their natural environment and conducted semi-structured interviews with 28 participants to understand stigma, barriers to acquisition, training, and design requirements. Half of the interviewees (50%, n = 14) did not feel disabled when using a walking stick, while 39% felt slightly disabled. 56% of the observed sample used non-medical-looking aids like hiking poles or umbrellas. Most interviewees (79%) purchased off-the-shelf devices, but less than half received seller support in choosing appropriate aids. The feelings associated with using walking sticks and similar devices are mostly positive. There is a preference in Hong Kong for using devices without a medical appearance to aid walking, such as umbrellas and hiking poles. There is a need to raise awareness of the risks of using umbrellas to aid walking and empower the user to make informed decisions when purchasing walking aid devices. In addition, there is a need to support the supply chain of walking aids, including umbrellas and hiking poles, to provide more information on device use, misuse, training, and maintenance.