Prolonged workplace standing is commonplace and associated with a range of lower limb issues. Evaluating footwear interventions aiming to modify plantar pressure during standing is essential as the body is static, creating a different requirement for footwear. Previous research associates medial midfoot pressure with greater perceived comfort and identifies arch height as the most variable element of foot shape. Targeting footwear mass customization within this area may better address differences within the target wearers. This study aims to evaluate a modular insole system for its ability to modify plantar pressure during standing. Twenty-five participants completed a static and dynamic standing protocol for 60 seconds whilst measuring in-shoe peak and mean plantar pressure (KPa) and contact area (%). Individuals wore three insole options targeted towards different medial arch shapes (A– low arch, B– medium arch, C– high arch) and rated them for comfort. Participants received guidance to self-identify foot shape (low, medium, or high arch). Comparisons were drawn across the three insole profiles and between the insole rated as most comfortable (preferred), and the insole that matched the self-identified foot shape (matched). As insole arch height increased, medial midfoot pressure and contact area significantly increased, alongside significant reductions in first metatarsal pressure and contact. Preference was spread across insoles A, B, and C (56%, 32%, 12% of participants, respectively). Sixteen participants had different matched and preferred insoles, with significantly greater medial midfoot pressure and contact in the matched insole. The modular insole enabled different wear experiences, however, results suggest that individuals selected insoles lower than their foot shape. Providing adequate medial arch support enables redistribution of pressure which may enable greater comfort during the workday.