Traditionally coming in leather or suede that rides up to the high ankle, the chukka boot is a handsome and all-around great men’s 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.
Chukka boots also go by the name desert boots, a type of military footwear that popularized this style. Desert boots were used by the British Army in many desert operations and then brought to the mass market via a certain Nathan Clark (of Clark’s shoe company), hence the deep association between chukka boots and Clark’s shoes. Technically, a desert boot is just a very specific type of chukka boot that has crepe rubber soles and traditionally comes in a light suede. In reality, desert boots and chukka boots are used interchangeably in modern men’s fashion.
The chukka boot combines the sturdiness of a boot and the smart-casual style of a low ankle shoe or trainer, making it an excellent investment for your footwear collection. As a work boot or part of a business-casual outfit, this is a versatile boot that provides just the right balance between practicality and style. If you’re looking for stylish chukka boots for men to wear during the Spring 2021 fashion season, then here are some of our favorites from across the web.
How Much Should You Pay for Men’s Chukka Boots?
Before we get into our picks for the best men’s chukka boots, we wanted to share a note on pricing. You can find chukka boots priced in the $50 to $90 price range; however, we would recommend spending at least $150 on these shoes. In our experience, the best men’s chukka boots cost about $200-$250, although there are some worthy options priced lower (see the Thursday Boot Co. Scout Boots below, for instance).
The best chukka boots, also known as desert boots, are made from premium leather or suede, which increases the cost. In addition, most of the boots below feature a Goodyear-welt construction, which provides waterproofing and durability. If you properly take care of your leather boots, they can last indefinitely, which is why these boots aren’t a one-season-and-done type of footwear. Even though you can find cheap chukka boots for sale, spending a little more is the wise decision.
Better to spend $150 or $250 on a pair of leather boots that will last for years to come than to buy a cheap pair of boots that will fall apart with moderate use.
1. Thursday Boot Co. Scout Boot
Thursday Boot Co. is known for handsome men’s boots that complement any outfit and aesthetic. The brand recently released a limited-edition motorcycle boot that we’re still drooling over. So, as expected, the brand’s Scout chukka boots for men lead the pack. We love the styling of this classic chukka boot, but what we really appreciate is that this pair of boots comes in 12 color options. All of the boots are made with premium leather or suede uppers, and slipping on these men’s boots will instantly elevate your outfit. Featuring waterproof and long-lasting Goodyear welted construction and a cork-bed midsole, the Scout boot will make sure that you’re comfortable and stylish for years to come.
Buy Thursday Boot Co. Scout Boot
2. UGG Dagmann Chukka Boot
Just look at it. 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
3. Cole Haan Original Grand Chukka Boot
Cole Haan is known for its appealing dress shoes that continue to challenge the status quo, and their chukka boot helps bolster this reputation. One of the most eye-catching features about this boot is the sole of the boot that takes on an athletic, sneaker-like appearance. Also, the Original Grand Chukka has a luxuriously cushioned sole that’ll comfort your feet during those busy on-the-go days. This style also comes in three colorways that are sure to pique your fancy.
Buy Cole Haan Original Grand Chukka
4. 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
5. Red Wing Shoes Work Chukka Boot
If you’re more interested in comfort than performance, then we’d recommend the Red Wing Weekender Chukka Boots featured below. However, if you need a pair of rugged work boots that can stand up to anything, you’ll want to go with the brand’s Work Chukka Boots. These traditional leather desert boots come with either a leather or suede upper. A full-leather footbed keeps your feet dry in wet conditions while also keeping your feet comfortable. However, these aren’t your typical pair of work boots, as they’re stylish enough for Sunday brunch, too. Contrast stitching and premium leather make these some of the best Chukka boots for men available in 2021. On top of all that, these men’s boots are made in the USA.
Buy Red Wing Shoes Work Chukka Boot
6. Sperry Cloud Authentic Original Chukka
A while ago, it was trendy to wear Sperry boat shoes during every season of the year. Now, the brand has a chukka boot that has the same evergreen qualities. It features vegan tan leather and a full-grain leather footbed which offers a more sustainable, polished look. With a shock-absorbing EVA heel cup and a Vibram rubber lug sole, this chukka has the potential to be your favorite option for any season.
Buy Sperry Cloud Authentic Original Chukka
7. Allen Edmonds Discovery Chukka Boot
For those of you who are looking for a sustainable option that’s hiking and business lunch appropriate, Allen Edmonds has you covered. This chukka has textured traction on the bottom that will help you keep your balance no matter the terrain. This boot comes in three colorways and says that you’re practical about your shoes and want a shoe that can do both — whatever that may be.
Buy Allen Edmonds Discovery Chukka Boot
8. TIMBERLAND Men’s Kendrick Waterproof Chukka Boot
BEST BEEFED-UP CHUKKA
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 Mens Kendrick Waterproof Chukka Boot
9. DR. MARTENS Men’s Sussex Chukka Boot
BEST FOR COMFORT
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?
Buy Dr. Martens Sussex Slip Resistant Chukka Boots
10. 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
11. Red Wing Shoes Weekender Chukka Boot
This option from Red Wing Shoes has all of the work boot qualities that Red Wing is known for but in a casual day-to-day option. Made with comfort in mind, the Weekender Chukka Boot features a full-grain leather upper, insole and cork midsole that will mold to your foot over time. The shoe should fit snuggly on your foot, with enough room to wiggle your toes. This is a perfect work or casual option that’s durable and stylish.
Buy Red Wing Shoes Weekender Chukka Boot
12. Banana Republic Suede Desert Chukka Boot
BEST UNDER $100
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 on 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 it doesn’t rain.