We all have those items in our wardrobe that seem to work harder than their counterparts. Trusty ankle boots are one such example, and we expect a lot out of them. In addition to comfort and durability, we require a certain level of versatility from the style—after all, we wear them from the office to cocktails to weekend jaunts all year round. The key is seeking out chic pairs that can be dressed up or down, in neutral hues with subtle details and, above all, an expensive-looking air about them. Whether you prefer flats or heels, leather or suede, here are eight pairs you’ll never want to take off.