Patients who sustain irreversible cartilage damage or joint instability from ankle injuries are likely to develop ankle osteoarthritis (OA). A dynamic ankle orthosis (DAO) was recently designed with the intent to offload the foot and ankle using a distractive force, allowing more natural sagittal and frontal plane ankle motion during gait. To evaluate its efficacy, this study compared ankle joint kinematics and plantar pressures among the DAO, standard double upright ankle-foot orthosis (DUAFO), and a nonorthosis control (CON) condition in healthy adults during walking. Ten healthy subjects (26 ± 3.8 yr; 69.6 ± 12.7 kg; and 1.69 ± 0.07 m) walked on a treadmill at 1.4 m/s in three orthosis conditions: CON, DAO, and DUAFO. Ankle kinematics were assessed using a three-dimensional (3D) motion capture system and in-shoe plantar pressures were measured for seven areas of the foot. DAO reduced hallux peak plantar pressures (PPs) compared to CON and DUAFO. PPs under toes 2–5 were smaller in DAO than DUAFO, but greater in DUAFO compared to CON. Early stance peak plantarflexion (PF) angular velocity was smaller in DAO compared to CON and DUAFO. Eversion (EV) ROM was much smaller in DUAFO compared to CON and DAO. Early stance peak eversion angular velocity was smaller in DAO and much smaller in DUAFO compared to CON. This study demonstrates the capacity of the DAO to provide offloading during ambulation without greatly affecting kinematic parameters including frontal plane ankle motion compared to CON. Future work will assess the effectiveness of the DAO in a clinical osteoarthritic population.