Just a minor bug, there probably isn't a goal trigger for that one so it always display's locked. It won't actually stop you progressing though so don't worry about it.
Interesting, I'll make a note of that and see if I can replicate. Though it might just be another quirk of the clothing system that'll have to be fixed in the overhaul whenever that happens.
I get where you are coming from. Hopefully once these characters have progressed down their stories I can focus more on filling in the gaps in a more general sense.
Try making use of the Jen time progression button. It'll take you through her activity slots where she will usually be available for something new (when she is at home anyway). Another suggestion is to check out the help/tutorial section on the computer, which will explain a few things, including the clothing system.
Once you've bought her a new outfit, you need to sleep and then she'll start wearing it (if it's low enough level). Then you should get new clothing event options in the kitchen for example, you use those to level up her clothing level.
I can only apologize that a lot of the early stuff is kinda janky. I was still very new to all this. Hopefully I'll get a chance to go back and fix it all down the line.
