Baggy/boyfriend jeans or pants should be hemmed or rolled up above the anklebone, and worn, says Elle, "with a tough, feminine shoe." Anne concurs: "You have to show some ankle with a baggy, or it just looks enormous and sloppy." No flats (unless you're totally casual and going for sneakers, in which case make doubly sure your ankles show and make triply sure that you don't look like a clown, which is a real and disastrous possibility). And no pumps, no kitten heels. The only possible boot is an ankle bootie (a tough, feminine one).
Illustration by Lauren Friedman