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Venous leg ulcer recurrence can be prevented with daily compression stocking wear; however, stocking effectiveness is often hindered by poor patient adherence. The ‘Personalised and Multi‐dimensional Compression Assessment and Intervention’ (PAMCAI) is a multidimensional decision aid, delivered by clinicians via an iPad application, designed to improve adherence. This study piloted the methodology and feasibility of PAMCAI's efficacy and cost‐effectiveness for evaluation in a larger randomised controlled trial (RCT). Using a two‐arm, single‐blinded pilot RCT with cost‐utility analysis, PAMCAI was compared with usual care in a tertiary hospital occupational therapy outpatient clinic. The primary outcome was adherence to wearing compression stockings, measured on a 4‐point scale. Twenty participants were randomised to receive PAMCAI (n = 10) or usual care (n = 10). Recruitment and pilot methodology appear feasible for use in a larger study. Compression stocking adherence was greater with PAMCAI compared to usual care (p = 0.002) and PAMCAI is likely cost‐effective, with an incremental cost‐effectiveness ratio of $3379.36 per quality‐adjusted life year (QALY) gained. Resolution of identified barriers to stocking adherence was positively associated with improvements in patient adherence. These findings support further investigation of PAMCAI in a larger RCT and its potential to improve patient adherence and the cost‐effectiveness of compression therapy for venous leg ulcer prevention.