It does? Just enter any item from the drop down menu and it will factor it in to your best work clothes. Nice to see if an item will help you at all, especially when having to choose between items from a quest. Ctrl+F + highlight all shows where they're used.
As for the skills side, it will show the base skill points only, so just chagne them accordingly, whether re-speccing or adding new pits, to see how choices will affect jobs.