Unless very poorly made, Sims have no problems sitting in a hoop skirt. The chair might disappear inside the skirt, but the front of the skirt should stay at or near the ankle level. There were a few Sims 1 hoop skirts which flipped up in the front, but I haven't seen anything for Sims 2 with the bone assignements that far off, including some stuff that I know was slapped together and put up for download!
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