An ankle boot is a must for any man’s wardrobe. Its low-cut silhouette is distinct, yet timeless, and pairs easily with just about any pant. Even better, an ankle boot isn’t overly fussy like a dress shoe or too casual like a sneaker.

This can’t-go-wrong style sits perfectly in the middle, making it super versatile. What this means guys, is that it’s definitely the type of boot that offers a lot of bang for the buck.

For instance, check out our men's ankle boot the Jefferson. This Two24 exclusive is our fresh take on a luxe, but really easy-to-wear ankle boot. Inspired by Ariat’s Rambler – a boot long popular for its mix of Old West ruggedness and modern flair – the Jefferson dials that up with a sleeker shape while hanging onto the worn feel of an already well-loved boot. Two24 achieves this signature look by using meticulously hand finished rich, Charles F Stead suedes and American Bison leather. And that means, the more you wear this boot the better it gets.

Like every Two24 luxe boot or shoe, the Jefferson is the best mix of high style and tried-and-true Ariat craftsmanship and comfort. This includes a medial zip closure (translation: placed in the middle just right) that makes the Jefferson easy to step into and out of in a flash. No doubt, it’s the perfect ankle boot for a get-up-and-go life.

As for dressing an ankle boot up or down, and looking smart either way, these are three of our favorite looks.

1. Three Easy Pieces + Ankle Boot = Instant confidence.

A crisp white shirt (simple), tailored blazer (of course), and slim black pant finished off with a versatile ankle boot as the ultimate closer. It’s a dressed up look that’s easy to wear so you feel relaxed, which is key to feeling confident. Plus (big bonus), it looks like you spent hours getting ready when you actually did it on foot dashing from that last minute meeting to dinner at 8pm.

2. Cargo Jacket + Dark Denim + Ankle Boot = It just works.

For this look a luxe ankle boot delivers the “3” in a 1-2-3 punch, which shows how easy it can be to pull it all together every day. Perfect for the office, a casual date, or wherever the day takes you.

3. Your Favorite Tee + Casual Pant + Ankle Boot = Simple and feels good.

Even a treasured tee shirt looks better when finished off with a luxe ankle boot. In this case, wearing denim with a slimmer leg usually works better. But we encourage you to experiment. For instance, in this pic the pant is looser fitting in the thigh yet slim in the calf so it still works.

There you go – three easy ways to wear a men’s ankle boot. Just remember that whichever way you choose to style it, and especially if you’re trying out a new look, walk with a bit of swagger.

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