Alright so I’ve figured it out a bit but a lot more work needs to be done. It’s a little complex but I’ll try my best to explain:
Using the example of the skirt, here’s what I did:
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Create the bone of the skirt on blender, with the bones matching the bones of the left and right left legs as well as the lower torso(UpperLeg, LowerLeg, LowerTorso). For now, we’ll call these bones LeftLeg, RightLeg, LowerTorso, with 5 bones in total.
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Once imported into studio, check to see if the deformation is working by rotating the bones and see if the mesh rotates accordingly.
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Parent the skirt into the character, resize and position appropriately.
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Connect the lower torso to the skirt with a Motor6D, and be sure to connect it in place, I used the Moon Animator Plugin - more specifically the Weld Edit.
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Reparent the bones to the specific limbs e.g. LowerTorso bone into the LowerTorso limb, you’re gonne need to mess around with the bone position once you do reparent.
Here’s the results:
https://gyazo.com/c302962b1976d24c1227cdc94da27d42
Some work needs to be done, but at least I know it’s definitely possible.