Chukka boots are the future of style, haven’t you heard? They achieve the perfect balance between business and casual. They look as good with a pair of Levi’s as they do with your best boardroom suit. They are a boot for all occasions, and no dude’s wardrobe should be without them. The best chukka boots are a sign of a man who knows how to put together his outfit and wear it with confidence. We all step into the new year wanting to improve ourselves and change our lives, so why not begin by enhancing your style? You’ve always felt stylish on the inside and now it’s time to prove it, so lace up and take a stride, we’re going on a fashion odyssey you won’t regret.
The Best Chukka Boots
Clarks Bushacre 2 Chukka Boots
The Clarks Bushacre 2 are our number one pick for the best chukka boots and with good reason. There ’s little about this most classic of designs we don’t like. It’s 100% leather, ensuring quality and durability, while still offering much-needed comfort. They suit both jeans and dress pants, giving you a variety of smart to casual and back to smart options.
As for the fit, the ankle design isn’t too high it will rub against you, but it’s still not advised to wear low socks, and the stitching around the heel is reliable. However, if you invest in this marvel of a boot, be sure to buy one size down for the most perfect, snug fit. If you want no-nonsense, straightforward boots, there are few better picks on the market. And if you need reliable boots for work, make sure you check our list of the best work boots on the market.
Clarks Desert Chukka Boots
Clarks are famous for developing some of the best chukka shoes you can find, and these Desert Boots are no different. Packed with history, they are the same style as those worn by British Officers during WWII, and even if you’re not feeling very regimental, they’re still a quality addition to any wardrobe, especially for those of you who just don’t jive with stuffy professional attire.
However, they run slightly smaller than other boots, and the canvas material isn’t waterproof, but they’ll still work fine as boots in Spring, Summer or Fall – just make sure you check the weather first. Despite this, you’re guaranteed reliable, durable, and sleek boots that are fit for all occasions, and as guys, that’s all we ever want, isn’t it?
Steve Madden Harken Chukka Boots
With a distressed finish, the Steve Madden Harken Chukka Boot provides something a little different and adds character to your everyday shoes. Inspired by the rebelliousness of rock ‘n’ roll New York City, you’re not only getting a boot filled to the brim with style and attitude.
Ideal for casual dress, you’ll still get away with them in more professional settings, while still offering you the comfort of everyday wear. Even though some customers claim they can be a little too small, if you get it right, you’ve got yourself a great pair of boots to strut your stuff, walk like a badass, and have people asking for your autograph, even if they don’t know who you are. The only other thing you’ll need is a pair of Wayfarers.
Timberland Earthkeepers Brook Park Chukka Boots
A famed and always reliable brand, no list would be complete without a shout out to Timberland, and it’s Earthkeepers Brook Park Chukka Boot is a sleek, stylish, and excellent professional boot for the young (or older) go-getter. The smooth leather is smart, while the linings are – remarkably, we think – made with 50% recycled plastic bottles. We’re realizing where the Earthkeeper name came from.
What we love the most about these Earthkeepers is the anti-fatigue technology, a perfect comfort solution for anyone who’s on their feet all day long. Furthermore, the exclusive Timberland Gripstick ensures traction, giving you peace of mind all year-round wherever you are in the world. As long as you order one size larger than your regular fit, this could be the answer to your office shoe problems for years to come.
Bruno Marc Urban Suede Leather Oxfords Desert Boots
If you’re looking for a bargain, the Bruno Marc Suede Leather Oxford Desert Boots are the best chukka boots you’ll find today or tomorrow (and probably after that, too) at such a great price. The suede leather construction is both flexible and comfortable, ideal for all-day wear at the office or out with your buddies.
The contrast stitching adds style, providing a dynamic appearance even when you’re not trying to stand out while the non-skid outsole also offers stability in a variety of conditions. They do run slightly on the large side, but as long as you know this, there’ll be no issues. Because of the material, it’s advised to take extra special care of them if you want to keep them in top shape for work or leisure. You’ll not get dates or promotions with scuffed up shoes, dude.
Dr. Martens Cabrillo Chukka Boota
If you’re looking for something a little more anti-establishment, a little more independent, a little more punk, then the Dr. Martens Cabrillo Chukka Boot is a quality option for you. They combine the smart-casual appeal of other chukka boots while maintaining the classic flair that sets them apart from other labels such as the iconic yellow stitching and heel loop.
The air-cushioned sole ensures comfort for all-day wear, which may come as a surprise to some, and will keep your feet cool in hot weather. They’re also well constructed, offering you reliability, however, the sole is maybe too thin for some, and you can feel the shape of gravel as you walk along the path. This isn’t a massive deal, but if you’re planning on doing a lot of walking there may be other better options available.
Bruno Marc Urban-06 Suede Leather Chukka Ankle Boots
Going for something unlike other designs so far, the laceless Bruno Marc Urban-06 Chukka Ankle Boots are a convenient slip-on pair for that on-the-go. They bring a casual feel to an otherwise hectic, fast-paced world, while still offering a timeless look that’s still sought after by many. The premium suede leather boasts sophistication, and suits a shirt and tie as much as it will a battered pair of jeans.
As for comfort, the flexible rubber sole and stacked heel ensure shock absorption along with durability, giving you a pair of boots that’ll last. However, reports on fit are conflicting, varying between true-to-size and a little tight, so remember that when you buy them and don’t give up on them if they’re not ideal.
Ferro Aldo Blaine Oxford
Boasting both style and a much sought after I Don’t Care attitude, the Ferro Aldo Blaine Oxford chukka shoes are a superb pair for anyone who likes boots that look like they’ve got a story to tell. Crafted to look worn and beaten as soon as you put them on, the Blaines go perfectly with a pair of black jeans, maybe a plaid shirt, and a guitar slung over your shoulder, while thousands of girls scream your name.
You might not have time for a rock ‘n’ roll dream, though, but whatever. You’ll still be itching to show them off picking the kids up from school, running errands, or running to the bank. They’re comfortable, durable, and the side zipper makes them easy to put on, which isn’t something other boots can claim too proudly.
Lacoste Sherbrooke Boots
With contrasting styles of leather, the Lacoste Sherbrooke Boots are an excellent smart-casual event option for those sick of dress shoes and who have been scolded one too many times for rocking your trusty Converse All Stars. They are lightweight and comfortable, with the ortholite insole giving you much-needed support for all-day wear.
The round waxed laces ensure they’ll not snap in an instant as lesser boot laces are wont to do, while the classic raw eyelets don’t distract from the casual style the boot is looking for. On the heel, you’ve also got an embossed Crocodile logo, so it should ease any worries about fakery. It may not be an acceptable dress shoe, but for all other occasions, the Sherbrooke is something that’ll you’ll be complimented on all day and all night.
UGG Leighton Waterproof Chukka Boot
Despite being more associated with college girls, pumpkin spice lattes, and sleeveless jackets, UGG is also known for developing rather stylish, rather brilliant boots for men. These chukka boots are an example of this and are our choice for the cream of the crop, the best of the best, and all other superlatives you can think of.
Waterproof, they’re suitable for any time of the year, and while you still must treat them with care, you won’t be half as worried about damaging them through carelessness. UGG Leighton Waterproof Chukka Boots are also comfortable, and above all well-constructed, giving you further peace of mind – especially considering the price. Despite some early teething (or walking) problems, they break in nicely, and once you’re done, you’ll never want to take them off, and we don’t blame you.
Chukka Boots Buying Guide
We’re sure you’re super excited to order your new chukka boots. Before you do that, though, check out this advice and information on caring for, maintaining, and breaking them in to ensure they last as long as possible, and that they don’t cause you blisters, which we all know is not what you want.
How To Maintain Suede And Leather
As stylish as both suede and leather are, they also take a lot to maintain. Unlike your standard polyester or canvas sneakers, shoes using either suede or leather (or suede leather) must be cared for properly if they are to continue looking smart, stylish, and not at all scruffy.
Before doing anything, though, you must treat your suede or leather boots with protective spray products that prevent water and stains from ruining them. This immediately reduces the chances of permanent damage and ensures you can wear your boots as often as you like. For consistent results, treat them with these protective products every one or two weeks.
Suede - You can’t always prevent dirtying and scuffing your boots, so to clean your boots, you need to first remove the laces then wipe away any mud and dirt gently using a shoe brush. This removes the loose layer of debris and allows you to focus on the more heavily soiled areas. For these, invest in a suede eraser to target specific areas where dirt has caked in.
However, you won’t always have this suede brush on hand, especially if you’re traveling and unprepared. For scuffs, you can run the boots against one another to remove them and get the boots to look as good as new. This sounds like an old wives’ tale but try it, the results might shock you.
If you don’t trust yourself to clean your precious boots, there’s always the option of visiting a professional who can give you further advice so for you to save cash.
Leather - If your Chukka Boots are of the leather variety, you must approach cleaning them in a slightly different way. You still remove the laces and remove any loose dirt, only this is done using a cloth and not a brush as the brush could scratch the leather.
After you’ve removed the bulk of the loose dirt, clean the boot with soap and warm water to break down any remaining dirt and wipe it over the boot. Once this is done, wipe it down again but this time with just a damp cloth (no soap, that part is finished).
With the dirt satisfactorily removed, you can dry your boots with a cloth, and then retreat them with the same protective spray you used initially, but make sure you do this in a well-ventilated area. After you’ve applied the spray, place the boots in a cool dry place, and be sure to keep them out of the sun or heat, as this could crack the leather and damage the boots for good.
Repeat these steps as often as you need to if you want to keep your boots in the best condition for as long as possible.
Breaking In Chukka Boots
Blisters suck. Despite this, we’ve all gotten ahead of ourselves by believing ‘Nope, won’t happen to me’. Unfortunately, we’ve also been proven wrong, finishing the day sore, aching, full of regret, and scared to put our new shoes on ever again. So what’s the best way to break in Chukka Boots? Well, there are quite a few options to consider.
Easy Does It, Bro - As much as you want to show off your boots as soon as they are unboxed, we all know this can end in tragedy and heartbreak. However, not all is lost, and you can still show them off, but only if you have a backup pair with you. You can take it easy breaking in your boots by wearing them in the morning when your feet are rested, and the weather is cool. It’s only in the afternoon, when things heat up when you should swap them out for an older, already broken in pair.
We’re not suggesting to carry an extra pair with you everywhere you go, but keeping another pair of boots at the office will help ease your feet into wearing the boots, saving you hours of pain, and ensuring you get the very best from your boots.
Crush, Smash, Squash, Or All of the Above - It might sound like something close to insanity for some, but crushing, smashing, or squashing the heels of your boots will do wonders for breaking them in while causing no damage to the boot itself. This technique softens the area where you will place the most pressure and therefore the area where you are most likely to get blisters, so you can wear them comfortably and without the risk of pain.
Protective Measures - Thick socks like those you use hiking are considered some of the best ways to protect your feet from blisters. Hiking socks are crafted to protect your heels from the rigors of walking long distances, but with your average new boot, these rigors are amplified. If you don’t want to invest in hiking boots (or can’t wait for them to arrive) you can get away with wearing multiple layers of socks as a stopgap, but this isn’t recommended for the long term.
Accept Defeat - If you’re more responsible than the average dude, then you can avoid blisters to begin with by purchasing blister pads before you even put on the boots. This prevents the chance of pain and means you can enjoy them from the moment you first pull them on.
- How to Wear Chukka Boots - The Trend Spotter
- How to Clean Men’s Suede Boots and Shoes - Live About
- How to Clean Leather Shoes and Boots - DIY Network
- How to Break In Your New Boots Without A Single Blister - GQ