For a multi garment outfit, I recommend a different simulation for each item starting with the innermost garment. In this case, the pink robe. Then if you chose, the yellow hood, then the red collar and then the blue hood. Have the robe collide with the figure and anything in the environment. With each new simulation, include the garments under it too. So the blue hood should include the yellow hood, the collar and the robe. For kneeling, I recommend starting with the figure behind where you want them to help smooth the skirts something like this.

and then to this

the blue square is only for reference of the location.

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