Michelle Ballet Flat, Christian Siriano Gold, $43, Payless Shoe Source
Perhaps named after our stylish First Lady, these classic keyhole flats are a wardrobe staple. These are wearable on all but the coldest days of the year, and would go with anything. Since I've been losing a lot of weight, I've dropped a shoe size and have to replace most of my shoes. I've bought a couple pairs of cheap flats but I need something nicer, and I think these will fit the bill.