Clothing Design's I'd like to see
Your list inspired me. I still haven't discovered any artistic talent in these genes so you'll have to manage with my description.
BTW: I have no experience in graphic or clothing design. Proceed at your own risk.
1. Line Art.
I like this idea. Black and white is classic. But I can also see blue with white lining. Like blueprints.
2. Front & Back Art
Using a Before and After theme, you could illustrate before on the front and after on the back to highlight the theme of your design.
3. Self-Improvement idea or motto
Then to connect your front- and-back line drawings to your theme you could run it along either the collar line or along the hem.
The Front would have a toppling tower of books. Maybe a small bespectacled character with a yardstick or broom attempting to stabilize the pile. The Back would have the character relaxing in a comfortable chair reading a book in front of a wall-sized bookshelf of books. Along the back hemline: ORGANIZATION.