Ankle BootsWhy they keep coming back: Said to have been inspired by the footwear of 19th-century soldiers, ankle boots are “easy for women of all calf sizes to wear―and you can get the look and the height of a boot without having to go full-length under trousers,” says Robert Verdi.
Keep them if: They’re “made from fine leather in classic colors, like black, brown, and dark blue,” says Finney, and any necessary rehabbing can be done easily at a shoe-repair shop.
Toss them if: They have an obvious faux finish, like lizard, which can make the boots seem cheap, or if “the toes are too pointy, which makes your feet look a bit funny,” says Charles Malka. And retire boots with studs, fold-over flaps, or other touches that scream of-the-moment fashion.
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