And here’s the problem, this person in charge of Michelle’s fashion is a caucasian female!
The first issue is that she’s female - as one of my friends put it, “Gay men make the best designers, cause straight men are too hung up on what they’d like to see women wear (which is usually a whole lot less than most women would wear) and women are too hung up on the kinds of clothes they’d wear themselves to stop and think about what looks good on other women”. Then, her being caucasian only exacerbates the problem, cause her being ‘too hung up’ on what she would wear extends to colors, and colors that someone with her skin tone could wear are not the best colors for Michelle’s skin tone since they’re drastically different.
IMO, the solution to this is for Michelle to hire Tim Gunn as her personal fashion advisor. I bet, with a bit of work, he could make her look at least passable. Then, he should hold “How to dress when you’re a part of international politics” seminar as part of the next G-20 type meeting.
I think you’re overintellectualizing this. My take - as a woman of the same age - is that the designer is ugly and wants other women to look ugly, too.