1. Good Clothes Well Worn:
Attractive, well-fitted clothes worn with confidence and deliberation
eg Hillary Clinton
After a long career of failures of dress, Mrs Clinton are now well-tailored classics of simple design and strong colours. She will never look great, but she looks as good as she can possibly look.
2, Bad Clothes Well Worn:
Ill-fitting, or ugly clothes that nonetheless project the desired image.
eg Justin Bieber
Often quite strange, borderline-trashy, badly fitting, clothes but warn with great charm and confidence, contributing rather than subtracting from, his effect.
3. Good Clothes Badly Worn:
Attractive, good quality and fashionable clothes worn without sense or understanding.
eg Michelle Obama
Mysteriously acclaimed dresser, Mrs Obama has a dream wardrobe budget; Unfotunately, she's assembled some good clothes that sit uneasily on her person and her role. Her hair is increasingly desperate and she seems to harbour delusions about her actual size.
4. Bad Clothes Badly Worn:
Ill-fitting, ugly, poor quality clothes worn without care or taste.
There is no shame in this category when you mean to be in it, but Madonna doesn't.