Ankle boots are the hardest working shoes you can own when the weather turns. They go with dresses, skirts, trousers and jeans, they handle a wet sidewalk better than most other styles and the right pair can be comfortable enough for a full day on your feet. Start with the heel. A low block heel is the most walkable, a stacked heel adds height without the wobble and a flat sole is best for weekends. The toe shape sets the tone. A pointed toe looks sleek and dressier, a rounded toe feels casual and a square toe is currently popular and comfortable. Material matters as well. Smooth leather is polished and easy to wipe clean, suede is soft and rich in color, and a zip or a pull on style is a personal choice. Look for a cushioned insole, a sturdy sole with some grip and shafts that hit right at the ankle so they sit neatly under a hem.

Ankle boots look good with almost everything, so the trick is to choose the balance you want. Pair a pointed black leather pair with a slip skirt and a knit for a sleek evening look, or wear a brown suede style with straight leg jeans and a wool coat for daytime. A lug sole boot adds an edge to a floral dress, and a low heel pair looks polished under wide leg trousers. Sock and hem length matter. Let the pants fall just over the top of the boot or use a slim ankle for a clean line, and try a cropped hem to show off the shape. To look after them, apply a protector before the first wear, wipe them after wet days and use a shoe tree to keep the shape. Rotate between two pairs if you can, so each has time to rest and last longer.