Flat or block-heel booties are some of the best for everyday style, pairing flawlessly with trousers, denim, and dresses. Look to other heeled types like a stiletto bootie, perhaps one with an eye-catching sculptural heel or a more modest kitten heel, for more dressed-up moments. Sock booties are most commonly associated with the ankle-grazing category—they tuck nicely under slim denim and trouser hems while cinching tightly to beautifully elongate legs with dresses and skirts.