Diabetic foot ulceration (DFUs) is increasingly prevalent in Singapore. Appropriate management is important since DFU brings with it an associated risk for lower limb amputations, high morbidity rates and costs. Footwear prescription has been a part of clinical guidelines to manage DFUs. However, adherence to prescription footwear is typically poor amongst patients. Reasons for this have been explored in Northern American and Western European studies, but not in Singapore's context. As cultural and climate differences limit transferability of findings from existing studies to individuals in Singapore, this study aims to explore the lived experiences of participants with diabetes using prescription footwear in Singapore.This was a qualitative study using interpretative phenomenological analysis (IPA) to understand some people's personal experience of using off the shelf prescription footwear. A total of 8 people with diabetes who received prescription footwear as part of their diabetic foot management were recruited. All participants provided written consent and took part in a semi-structured interview lasting up to an hour. Interviews were digitally recorded, transcribed and analysed using an IPA approach.The analysis identified the super-ordinate themes of 1) security and 2) acceptance with sub-themes of 1.1) risk and 1.2) protection and 2.1) personal and social acceptance and 2.2) social and cultural acceptance respectively that inter-related to influence how participants' made footwear decisions. This process of evaluation was portrayed to be a fluctuant one, making it difficult to predict yet necessary to understand. A modified seesaw model of adherence is suggested to explain this decision-making process.The complex manner by which participants grappled with security and acceptance is often overlooked when footwear is prescribed, highlighting a need for a more collaborative clinician-patient partnership for these issues to surface in clinical practice. Furthermore, prescription footwear should be seen more holistically. Empowering patients with choice to select from a range of therapeutic yet normalised footwear could increase the level of security and acceptance they experience with its use.