The study sought to investigate whether an orthotic stiletto could modulate the pressure and comfort under the forefoot, arch and heel that stiletto wearers experience. Twenty-two women participated. We measured the peak pressure and pressure-time integral for orthotic stilettos with built-in metatarsal pad, heel cup and arch support; standard stilettos without inlays; and trainers. Comfort was recorded during 3 × 3 working days. The orthotic stiletto exhibited lower metatarsal head1 (MTH) and MTH2+3 and heel pressures than the standard stiletto (p < .01), and a long second metatarsal increased MTH2+3 pressure (p < .01). The comfort in the forefoot and heel was higher in the orthotic stiletto than in the standard one (p < .01), and comfort in the forefoot was correlated to the pressure-time integral of MTH2+3 (p = .03) and not peak pressure. Off-the-rack orthotic stilettos can notably reduce plantar pressures and improve forefoot and heel comfort during everyday use. Practitioner Summary: Off-the-rack orthotic stilettos with built-in metatarsal pad, arch support and heel caps can lower the pressure under the heel and forefoot in comparison with a standard stiletto and can improve comfort during everyday use. Having a long second metatarsal is a risk factor for increased forefoot pressure.