>>270929396
>but that looks really time-consuming if there's not one parent you can just add it to.

Dynamic bones have an exclusion feature, so you'd put the parent on the hip, and then exclude every thing under the hip that isn't the skirt bones. Also with dynamic bones comes the dynamic bone collider feature. You can put colliders that your dynamic bones will interact with. Putting these colliders on your hips or upper part of your legs for example, could push your skirt out which would help make it not clip as much.

>Is weight painting something especially hard to do? I'd like to just be able to get models working properly without clipping like that.
If you're just foraying into blender and uploading avatars for the first time into VRChat, then yes it's probably something you might have a tough time grasping.