The Best Chukka Boots For Men 2020

The Chukka boot is an amazingly popular boot for men and for good reason, it’s a great casual shoe you can wear and get away with in pretty much 90% of situations.

It’s an easy way to casually dress-up without looking out of place. Chukka boots are the perfect footwear in-between casual sneakers and full on fancy boots.

If you find yourself wanting to be more dressed-up or business casual (so no sneakers) but don’t want to look overdressed with dress shoes or some full on ankle boots, I highly recommend you get yourself a pair of Chukkas.

Here are, in my opinion, the best chukka boots on the market in 2018.

1. Clarks Desert Boots

$: Clarks Suede Desert Boots

The undisputed champion of chukka boots – you get the style and great quality for an unbeatable price. If you’re not sure how you’ll like chukkas, trying on a pair of Clarks is a pretty risk free way to determine where you stand (no pun intended).

2. Red Wing Heritage ‘Weekender’ Chukka

$$: Red Wing Heritage Weekender Chukka

If you’ve ever researched buying some sturdy boots, you’ve come across the brand Red Wing Heritage. They’re known for their amazing quality in the boot world.

When you buy a pair of boots from Red Wing Heritage, you know you’re getting the very best handcrafted boots money can buy, which brings me to my next point – they can be a little pricey.

You truly get what you pay for with these boots though, the slimmer profile and the high quality make is very hard to find in a cheaper boot.

To many these boots are an ‘upgrade’ to the Clarks chukka boots, both in looks and quality.

3. J.Crew Macalister Chukka Boot

$$: J. Crew Macalister Suede Chukka Boots

J Crew surprisingly makes a very fashionable chukka boot. The boot is made in Italy with Italian grade leather so you know you’re getting some top quality stuff.

The style is very modern with a slimmer profile than your average chukka boot. The boot is also unlined to give it a more casual feel.