General questions from a complete novice - Process of making clothing and armor

I did enable physics both in the Asset Details panel of the Mesh and the Cloth tab but it still results in the issue as you can see in the attached image. The moment I press “Deactivate Cloth Paint”, it does simulate cloth physics over the painted area but doesn’t actually “stick” to the animated body.

One thing that I might possibly be doing wrong is that both cloth and “body” mesh have the same physics asset. I also didn’t do the initial animation with the cloth attached.
Could any of this be resulting in the issue?

Thank you for your help!