arXiv:2610.32143v1 Announce Type: new Abstract: Robot-assisted dressing is particularly challenging due to narrow openings and articulated body parts. Even small errors in the relative pose between the body part and garment opening can cause snagging, missed insertion, or incomplete dressing. To address these challenges, we formulate dressing as a geometry-aware insertion problem that represents task-relevant spatial relationships between the body part and object opening, rather than relying on the full deformable-object state. Based on this formulation, we propose a Reinforcement Learning (RL) framework combining a staged curriculum, which progressively guides the policy from coarse alignment to insertion and final placement, with a finger-wise insertion soft gate that provides continuous feedback on individual finger insertion progress and helps suppress premature insertion. We evaluate the framework on rigid and deformable bracelet dressing tasks through component ablations, systematic variations in the initial hand pose, and closed-loop execution of the learned policies on a real robotic system. On the post-training deformable evaluation, the full method reaches 84.7 +- 1.2% success. The insertion gate accounts for the largest gain, and adding the curriculum on top of that gate reaches the top score. On a mannequin hand the same full policy succeeds on 15/20 real-robot trials.