If I were to set about to create a wardrobe that accented one's flaws and minimized one's advantages, it would be Michelle's Closet.
You don't wear shoes of that category with JCrew.
Desiree Rogers, her "Commes des Garcons-wearing" Social Secretary was often seen at fashion shows (weekdays on the dime) sitting between editors of big fashion mags..I suspect it was all for Michelle as well, and not just about Rogers own "preening and self-indulgent" ways.
I do admit they need not dress in rags and loafers..but at least seek help from stylists like Rachel Zoe.