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Julia, I too found some of the renderings of Michelle Obama questionable and also troubling because of their subtle use of stereotypical imagery. Christian Lacroix's Michelle is a sneering, mean-looking lady, much like the "angry black woman" the Obama haters accused Michellle Obama of being. Why is she frowning in every sketch? Doesn't she have every reason to be happy? After all, her husband is the soon-to-be leader of the free world. You'd think the new first lady is smile-challenged. Same goes for Zak Posen's scowling, slouching Michelle, an obviously sullen black woman. They might as well have thrown in the controversial New Yorker cover sketch of Michelle as black militant for good measure. Betsy Johnson's sketch was a bit too graffiti-artisty for my taste. Maybe Johnson was going for whimsical, but it seemed to me that she was trying for an urban (read: black, or inner-city) look. Her Michelle looks out of sorts with the crazy big hair and all those distracting handwritten notes surrounding her; they might as well be graffiti tags spray-painted on a wall. While some of the designs were indeed gorgeous, some of the drawings of Michelle's facial feautures were so suspect that they drew attention away from the dresses.
And by the way, the other black female nonmodels to grace the cover of Vogue were Marion Jones (2001), Jennifer Hudson (2007), and Oprah Winfrey (2007).* Vogue Editor Anna Wintour only let Oprah appear on the cover after she agreed to lose weight first. I can't believe Oprah, media powerhouse Oprah, even agreed to such nonsense.
You're also right, Julia, about the fashion world being inhospitable to black women. That's why my radar always goes up when I see questionable pictures or drawings of black women. If Michelle does land on the cover of Vogue, I hope they won't try, and I bet she won't allow them, to depict her in the same way they did Jennifer Hudson: slightly bent over with her mouth open wide, hair flying, and ample cleavage on view. Think loud, fat, black woman. Annie Leibovitz and Vogue were rightly criticized for the photos.
I've seen this sort of thing too many times for it to be a concidience. Just take a look at any of those obnoxious bridal magazines and notice how the women of color—the few token black and Lationo models even in the mags—are photographed. They are often wearing the more revealing dresses, their mouths are usually open or pursed in suggestive fashion, their makeup is heavier, and their hair is sometimes styled to suggest wild-haired raven. The subtle suggestion is that they are looser, or whore-light, and the imagery is stark when compared with the prim and proper, virginal-looking white models photographed with their hair done up in sophisticated buns.
You asked if it was hard to draw a woman with black skin, and I think the answer is no, at least not for those artists/designers who don't reflexively see, and thus imagine, black women in a stereotypical light.
Correction, Dec. 12, 2008: The original sentence included only Hudson and Winfrey.