You physically can’t trot around in skyscraper heels 24/7, so flat shoes are a necessity—especially the ladylike kind that you can wear on the street, with a dress, on a lovely spring day. But if your feet are on the large side, choosing flats that flatter can be a challenge. A pointy toe is out (it adds length), as is patent leather (shine = volume). To the rescue: The calfskin cap-toe ballerina pictured here. Its light flesh tone matches the pasty legs of a typical Chicagoan (of Irish heritage, anyway) emerging from her winter cocoon, and the rounded black cap toe visually shortens the foot. While Chanel makes the classic version, I prefer the Prada, which has a somewhat sturdier feel—and somewhat kinder price. It’s the best friend a bigfoot ever had.
$550 at Neiman Marcus, 737 N. Michigan Ave., 312-642-5900