@sozobe,
Random-ish selection of stuff I've liked:
I like the pop of color here, the highness of the belt doesn't bother me, seems to be the right place on her body.
Love the skirt and the boots.
Hard to look that good in athletic wear!
I like the full, interesting skirts with the fitted tops, obviously.
LOVE the purple shoes with this dress!
I agree with these 10 selections, the pics are big(GER) though so I won't post them here:
http://www.thesun.co.uk/sol/homepage/woman/fashion/3362966/Michelle-Obamas-Top-10-dresses.html
Overall point -- I think that when she takes fashion risks, and is in the public eye pretty much every day, there are going to be some misses. But I approve of the risk-taking as a concept and I think there are also a lot of hits, and personally I like her style.