Daily living activities present a diverse array of task and environmental constraints, highlighting the critical role of adapting gait initiation (GI) for an individual’s quality of life. This study investigated the effects of GI directions, obstacle negotiation, and leg dominance on anticipatory postural adjustments and stepping kinematics. Fourteen active, young, healthy individuals participated in GI across 4 directions—forward, medial 45°, lateral 45°, and lateral 90°—with variations in obstacle presence and leg dominance. Results revealed a consistent decreasing trend in maximum center of pressure displacement, anticipatory postural adjustment duration, step distance, and swing leg velocity with lateral shifts in GI directions, yet the step duration and swing leg heel trajectory were not affected by GI directions except in lateral 90° GI. Center of pressure displacements were intricately scaled to directional propulsive forces generation, and the stepping kinematics were influenced by the directional modifications in movements. With obstacles, modifications in anticipatory postural adjustment metrics and stepping kinematics reflected the obstacle clearance movements. The dominant leg GI exhibited longer step durations and greater movement variability in medial 45° GI. The current investigation of GI factors expands our existing understanding of GI dynamics and offers valuable insights applicable to fall prevention and gait rehabilitation strategies.