The Chukka Boot Has Unlimited Styling Potential — Here’s Why We Refuse to Take Them Off

best Chukka Boots for men
Courtesy of Zappos
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Traditionally coming in leather or suede that rides up to the high-ankle, the chukka boot is a handsome and all-around great boot that goes great with nearly any outfit. Generally, the sole is made from either rubber or hard leather. It is the ankle boot’s younger, more city-friendly cousin. Having said that, there is such a fantastic range of chukka boots out there that a chukka boot could suit most of your footwear needs very well –– from dining out to digging up dirt. But what it does really, really well is that ubiquitous, smart-casual blend we know and love so well.

Down to the nitty-gritty and there is a subset of the chukka boot that goes by the name of the desert boot. It was used by the British Army in many desert operations and brought to the mass market, via a certain Nathan Clark (of the Clark’s shoe company), hence the deep association between chukka (desert) boots and Clark’s shoes. In reality, the desert boot is just a very specific chukka boot that has crepe rubber soles and traditionally comes in a light suede.

The chukka boot combines the sturdiness of a boot and the smart-casual versatility of a low ankle shoe or trainer, making an excellent investment. Here are some of our favorites from across the worldwide web.


1. UGG Dagmann Chukka Boot


Just look at. It is a thing of complete and simple beauty. It comes in a supple leather or suede upper and a flexible, Treadlite and rubber sole, giving the wearer ultimate ergonomic satisfaction. Wear with some quality, dark denim jeans and you will be well on your way to getting the perfect smart-casual look.

UGG Dagmann Chukka Boot - best chukka boots for men Courtesy of Zappos

2. TRASK ‘Brady’ Chukka Boot


Presumably named after one very lucky Brady out there somewhere, this boot captures the utility of a good dining out shoe: smart-casual and easy to throw on without too much thought. It is constructed from a supple leather which makes for an extraordinarily comfortable wear.

TRASK 'Brady' Chukka Boot, best chukka boots for men Courtesy of Nordstrom


3. Goodfellow & Co Jahlin Boots


You don’t have to break the bank to look handsome in a pair of chukka boots. For all of our modern footwear needs on the cheaper end, we’re constantly looking at Target to hook it up. These chukkas from Target’s Goodfellow & Co brand are a handsome option to sport on any date, interview or casual day for just under $50. We consider these a great starter option for any guy looking to test out the style, but can’t decide whether or not it’s right for him.

Goodfellow & Co™ Jahlin Boots Courtesy of Target

4. SOREL Madson II Waterproof Chukka Boot


These chunky, treaded soles are going to make easy work of a countryside walk, a mountain hike or just the farmyard chores. But then again, would you really want to cake these in mud, or scratch them? If we were you, we’d just pose around town in them, but that’s just us.

SOREL Madson II Waterproof Chukka Boot Courtesy of Nordstrom

5. ASOS DESIGN Chukka Boots


Merged with the handsome black leather look typically seen in loafers, these chukka boots are a fancy (yet affordable) way to step up your formalwear look in style. At just under $60, buying these black leather boots won’t even break the bank. They’re smartly designed and good looking enough to give the pep in your step you need.

ASOS DESIGN Chukka Boots Courtesy of ASOS

6. TIMBERLAND Men’s Kendrick Waterproof Chukka Boot


This boot is versatility made flesh (er, leather). It comes in a lovely deep brown full-grain leather with brass fittings, giving it a smart, formal feel to it. In combination with the grippy sole, it will work just as well in a high-class restaurant as it will hiking, or navigating harsh winter weather on East Coast streets.

TIMBERLAND Chukka Boot Courtesy of Amazon

7. DR. MARTENS Men’s Sussex Chukka Boot


You will be extremely hard-pressed to find a more comfortable shoe than this. The air-cushioned Dr. Marten sole is one of the softest and coziest around. Plus, the iconic yellow stitching that circumnavigates the shoe is pure class. Channel the inner punk, but in like a very bourgeoisie way, you know?

Dr. Martens Chukka Boots Courtesy of Amazon

8. Acne Studios Black Chukka Desert Boots


We love the chunky yet sleek simplicity of these boots. The vertical grating details on the mid-sole, give a nice angular, modern inflection, as well as the deep black shine. They are constructed of a polished calfskin to get the striking look you see below and they’re finished with a fashionable thick lace-up closure. These boots aren’t made for just anyone, though. We suggest these for the kind of guy that puts tons of effort into his daily ‘fits. And if you’re the all-black kind of outfit wearer, look no further than these babies.

Acne Studios Black Chukka Desert Boots Courtesy of SSENSE

9. UGG Neumel Chukka Boot


Merge the chukka style with the comfort from the world’s coziest slipper: the UGG. Given another UGG sits in our first choice, you should know the brand well by now. Or, if you have a daughter or personally went to middle or high school from the years of 2006 to 2016, you know what these babies are all about. They were popular, to say the least. So, get a pair for yourself and find out what all the fuss was about. You’ll get it. And, if this brown color pick isn’t for you, you’re in luck. There are 11 more to choose from.

UGG Neumel Chukka Boot Courtesy of Nordstrom

10. Redwing Heritage Weekender Chukka


These are fantastic weekend shoes. When fresh out the box they will work well in a smart-casual setting. But the real reason we love them is the color combination of the brownish copper with cream/beige in the sole, stitching details and the duo-chromatic laces. Redwing is famed for their sturdy work boots, so rest-assured these will have a rigid build quality and a long shelf-life.

Redwing Heritage Weekender Chukka Courtesy of Redwing

11. Banana Republic Suede Desert Chukka Boot


So, you thought the chukka boot was just good for zipping up and down mountains, plowing through snow-filled streets and hanging out with your pals? Well, this pair from Banana Republic is certainly not. These are an excellent and very stylish alternative to an oxford or derby shoe, that’ll be sure to impress in first dates and job interviews alike. They’re made with a handsome sandy suede to keep you looking dapper no matter what the day brings — just hope that isn’t rain.

Suede Desert Chukka Boot Courtesy of Banana Republic

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