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One of the best—and most fun—ways to update your fall wardrobe is with boots. Of course, with all the options available, it can be overwhelming. How many pairs do I need? What style should they be? What can I wear them with?

Garmany’s fashion experts share the basic boot styles every woman needs in her shoe wardrobe, all of which are on-trend but classic enough to be worthwhile investments:

1. An everyday riding boot. These bad boys in a neutral color like brown, camel or black will be your go-to with jeans or dresses. Stuart Weitzman has an extensive collection of riding boots for fall/winter.
2. An ankle boot. Perhaps the most versatile shoe in the boot family, ankle boots, like Carven’s, pair well with jeans, slacks, midi-skirts and dresses.
3. A stiletto or platform booty. Whether you choose a stiletto or a chunkier heel is up to you, but you’ll want a pair of “fancier” booties—Rebecca Taylor has some great ones—that you can wear to work or for special occasions.
4. An over-the-knee-boot. For those days when you want to put a little more fashion into your step, wear an over-the-knee pair from Aquazurra in suede or leather with mini skirts or over jeans.