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Men's ankle boots are one of the most versatile categories of fall footwear. Whether you're looking to elevate a casual outfit of jeans and a sweater or want to give your suit a little swagger, go for a pair of Chelsea boots, chukkas, zipper boots, Jodhpurs, or plain or cap-toe boots. Any of these styles will accentuate the length of the leg, and give you a bit of added height, all with a refined sensibility that helps unify your look.
A real standout in this roundup is the Taft Dylan boot, which is unique without being over the top. It's handcrafted in Spain using Italian leather and Blake stitching for a comfortable fit and easy resoling. Taft's boots, beyond their stellar looks, are also super comfortable. Another obvious winner is the Blundstone Chelsea boot. We've included the dark green version, which besides being handsome enough for a night out, is built to take on harsh conditions, so you don't have to fret when faced with rain, snow, or mud.
While the boots in this roundup use standard men's sizing, many brands offer inclusive sizing. The styles you'll see here can suit anyone, but if you're looking for smaller sizes, see our guide to the best ankle boots for women.