First, let's just say that to all the hypercritical comments made about Michelle Obama's personal style, I say, "BOOOOOO". Yes, "BOOOOO". Damnit, I LOVE HER STYLE.
Michelle Obama represents something that I completely understand: She has the personal style of a smart, well-educated, tall, curvy 40-something woman who had a professional career before becoming First Lady. She is clearly a thoughtful, creative woman who loves to express herself, and is interested in looking cool and hip, but age- and situation-appropriate. She has had to dress for herself, not for a role as "political" wife, like Nancy Reagan or the Bush women.
I think Michelle Obama's personal style reflects a generation that, while not second-wave feminism, is also not Hillary Clinton's late 60's Wellesley feminism, either. To a degree, Hillary's generation had the luxury of not really caring that much about how they looked--it was important to break the stereotype in order to further women's goals. I understand that, and I applaud it. I think that's why Hill had such culture shock in the 90s when the media was attacking her style (or what the media perceived as a lack of style). Hillary is old enough that she was on the further side of the "what you wear doesn't matter" curve.
Michelle, on the other hand, is a year younger than me, and hence, is on the backside of the "What you wear doesn't matter" curve. She was clearly raised by a mom who took pains to say to her daughter, "There is a way you look, and there is a way that looking good says something to the outside world....that you want to be taken seriously." (I won't delve into the race issue, but I can only imagine that it was twice as important for Michelle to present an exterior that was perceived as professional and competent.) Further, I suspect that her mother also raised to her make the most of what you have. I don't know Michelle or her mother, but I get the feeling that Michelle never thought to herself, "Oh, well Barack has become President. I think I'll throw out all my old clothes, and buy new, American designer togs that are boring, cookie-cutter over-the-top pieces of crap which don't reflect my style at at all."
Which brings me back to my initial comment: I loooooove her look. If I were 30 pounds lighter, I'd be buying half the stuff she wears. I love it. Alaia, Thakoon, J. Crew, Talbot's....what a great blend of funky and classic. She has high-low style down pat. It rocks. Screw all of you who say, "You don't wear a cardigan to meet the Queen!" Did you see the crap-ass, poorly-fitted dress that Mrs. Brown wore? And she wore black tights with it! Mother of god!
Donatella Versace has been quoted as saying, "Wear what you like, and wear what looks good on your figure...that's style." And I agree. Michelle is controversial in the fashion press precisely because she wears what she likes.
I also credit her with the resurgence in day dresses, of which I bought two this weekend. My mother is thrilled. For all the time when I as young, and she tried to get me to wear dresses I say: Mom, patience is a virtue. I think she thought I'd spend the rest of my life playing in the mud, wearing oversized flannel shirts and cords.
So Mommy and Michelle, these are for you!