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

best mens chukka boots
Courtesy of Huckleberry
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Traditionally coming in a leather or suede that rides up to the high-ankle, the chukka boot is handsome and all-around 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 world wide web.


1. UGG Camino Water Resistant Chukka Boot


Just look at. It is a thing of complete and simple beauty. It comes in a supple leather and a flexible, synthetic Treadlite 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 CHUKKA BOOT Courtesy of Nordstrom


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 suede which makes for an extraordinarily comfortable wear.

TRASK CHUKKA BOOT Courtesy of Nordstrom


3. SOREL Madson Waterproof 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 Chukka Boot Courtesy of Nordstrom


4. CLARK’S Desert Boot


Get a claim on wearing the original desert boot design, with a contrast natural crepe sole, just as the original should be. We love this boot in black 100% leather suede, it gives the shoe a real panache and formality that is useful for dressing up for a night on the town.

Clark's Chukka Courtesy of Need Supply


5. TIMBERLAND Men’s Kendrick Waterproof Chukka Boot


This boot is versatility made flesh. 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


6. 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


7. TOD’S Nubuck Desert Boots


We love the chunky simplicity of these boots. The vertical grating details on the mid-sole, give a nice angular, modern inflection, as well as the black and red-brown coloring. They are constructed of a supple nubuck leather and the soles are inspired by the brand’s famous gommini (slip-on shoe), providing ample grip when things get challenging.

Tod's Chukka Boots Courtesy of Mr Porter


8. BRUNELLO CUCINELLI Shearling-Lined Suede Boots


What could be more satisfying than putting your feet into a shearling lined boots before heading out on your winter errands? These boots look the part –– they come in a supple suede that will only soften, breakdown and become more comfortable with wear. The chunky lug rubber soles have your traction woes cover, too.

Brunello Cucinelli Chukka Boots Courtesy of Mr Porter


9. REDWING HERITAGE Weekender Chukka


These are fantastic all-rounder 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 olive brown with cream/beige in the sole, stitching details and the duo-chromatic laces. Redwing are famed for their sturdy work boots, so rest-assured these will have a rigid build quality and a long shelf-life.

Redwings Chukka Boots Courtesy of Redwing


10. RHODES FOOTWEAR Felix Chukka


So, you thought the chukka boot was just good for zipping up and down mountains, ploughing through snow-filled streets and hanging out with your pals? Well, this pair from Rhodes Footwear definitely changed the way we perceived the chukka boot. 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.

RHODES FOOTWEAR Chukka Boot Courtesy of Huckleberry