Found something accidentally while playing the latest build.
While talking to Cassie, I accidentally pressed the option to change her clothes and without much of a thought I hit the back button. Instead of backing out of the dialogue, it changed her into her island outfit and just repeated the Dress Ragged, Dress Clean options. Pressing the Done option works as intended, but will keep Cassie in her island outfit. Changing back to her Ragged and Cleans works seems to work just fine.
Doing some snooping with the other two, I found that this is only possible with Cassie and it is easily repeatable.