Chukka boots are a versatile shoe that suit any occasion whether you’re expected to dress mostly formal or if you’re just having a few drinks at the bar with your friends. With a refined style, they you can mix and match them with a pair of Levi’s and a flannel shirt, or go a little more stylish and wear them to the office with a pair of dress pants or chinos. The best chukka boots are comfortable enough for anyone who needs to stand all day long while also maintaining the sleek, modern style that still retains the classic look that shows you’re someone who knows how to dress.
The Best Chukka Boot
The indisputable pick for the best chukka boots, the Clarks Bushacre 2 are a timeless and versatile option for all occasions boasting superb craftsmanship and durability, a comfortable fit, and a mixed construction to provide both breathability and moderate waterproofing.
The high-quality materials are one to rely on, although this means they may take a while to break in compared to other boots. The double eyelet lace design is modest, while the metal ringlets protect both the laces and the shoes from marring and tearing. Make sure you also check our guide to the best trail running shoes for men.
Two eyelet lace-up front
Cushioned insole for a comfortable fit
Leather and suede mixed construction
Stylish cuts and reliable stitching
- ModelBushacre 2
- Weight12 ounces
Well made with superb construction
Smart style suitable for multiple occasions
Take a while to break in
An excellent and upper-range pair of men’s chukka boots, Steve Madden Heston are 100% leather for reliable waterproofing while also boasting a synthetic sole to optimize comfort for both casual and close-to-formal events. This soft padding ensures easy all-day wear, while the leather is easier the break-in than many similar styles.
While delivering a sleek and modern style, the traction ensures it’s capable of handling a variety of terrains to ensure you keep on your feet, even though it’s a little heavier than other options so could cause fatigue. Our handy guide to the best high tops features more great products like this.
Lined around the edges with leather
Soft pad for comfort helps with all-day wear
Good traction on sole for variety of terrains
Sleek and modern style keeps a classic appearance
- BrandSteve Madden
- Weight5 pounds
Rich, smooth leather dressing up or dressing down
Leather quickly relaxes for simple break-in
Great arch support to ensure comfort and reduce strain
Slightly heavy compared to other shoes
As for our best value pick, the Ferro Aldo Blaine Oxford is a deceptively superb shoe at a fantastic price perfect for those who need a smart pair of waterproof chukka boots on a shoestring budget. The synthetic leather construction looks the part and provides essential breathability and comfort while the double stitch and waxed shoe laces provide an all-round durability.
It’s also the only pair with a zipper to help you easily get them on and off while also giving further options to let your feet breathe. They run a little narrow in the toe box, but buying a size up should solve this. Be sure to also check out our list of the best trail running shoes for women for more great items like this.
Superb hand-crafted synthetic leather construction
Waterproof design keeps your feet dry
Durable and breathable design provides comfort
Zipper ensures boot is easy to remove and put on
- BrandFerro Aldo
- Weight1.05 pounds
Waxed shoelaces last for longer
Double-stitch ensures durability and long life
Produced using 100% vegan-friendly materials
Runs slightly small with a narrow toe box
Segueing from leather to suede chukka boots, the Kenneth Cole Reaction Desert Sun is a smart summer shoe suitable for a variety of environments. The low-cut profile ensures they’re not too garish and distract from the rest of your outfit, but the lace-up close still delivers that sophisticated look you expect.
With a flex rubber sole, you’re guaranteed all-day comfort while also getting essential durability even after wearing them all summer long. The suede isn’t waterproof, but you likely knew that, so just stay away from dark clouds and famously wet nations, cough England cough. Love shoes? Check out our review of the best white sneakers for our top picks
Low-cut profile with 3 blind eyelets and striped midsole
Lace up closure for a more sophisticated look
Cushioned insole for easy all-day wear
Stitch out construction provides extra support
- BrandKenneth Cole
- Weight12 ounces
Durable, flex rubber sole ideal for those on-the-go
Premium suede upper is suitable for office and casual environments
Large sole enhances comfort
Suede material isn’t waterproof
Old punks will love the Dr. Martens Cabrillo as yet another chance to stick it to the man. The tough leather is durable and waterproof and comes readily creased for an immediately broken in look.
The rubber sole provides a comfortable feel regardless of whether you’re enjoying a family BBQ or moshing with your old pals in the pit. They aren’t available in half sizes, so you’ll need a size larger for optimal comfort. Find more great products like this by checking out our guide to the best basketball sneakers.
Provides perfect broken in look before wearing them
Leather construction is durable and waterproof
Rubber sole provides comfortable feel on different surfaces
Classic pull-back tab on Achilles for easy pull-on and off
- BrandDr. Martens
- Weight1.3 pounds
Sidewall construction stitched and cemented to base of upper
Lightly cushioned textile footbed
Excellent price for superb durability and reliability
Not available in half sizes so buy a size larger than usual fit
The Rockport Classic Break are a top of the range option for those who love their chukkas boots more than anything else. The comfort comes from an EVA footbed, while its TR outsole ensures grip and stability on a variety of surfaces.
It’s also one of the most lightweight shoes around while still delivering excellent shock absorption to reduce strain on the heels and balls of your feet. The colors are a little off from what you see in pictures, but we’re sure you can make it work, regardless. Don’t forget to check our guide to the best stability running shoes.
EVA cushioned footbed conforms to shape of foot
TR outsole ensures great grip on a variety of surfaces
Soft-knitted fabric lining is comfortable and easy against the foot
Textile lining offers breathability to handle all-day wear in multiple environments
- ModelCLASSIC BREAK CHUKKA
- Weight1.2 pounds
Flexible leather makes walking easy and straightforward
Suitable for a variety of functions and occasions
Lightweight shock absorption is easy on the heel and balls of feet
Color in pictures is not always accurate
Smart and to the point, the Calvin Klein Ulysses Suede is an unassuming shoe perfect for casual office environments all year-round. The blind eyelets keep its appearance simple, while the suede upper provides the sophistication necessary for moving up in your business.
They’re easy to break in within a few hours of wear for simple comfort, and the laces are long to provide a secure fit, however, these run almost 2 sizes larger than standard, so to avoid looking like a clown, make sure you don’t go with your usual size. If you like working out check out our guide to the best crossfit shoes.
Blind eyelets provide a more modest appearance
Synthetic lining and insole ensures comfort and prevents itching and abrasions
Man-made outsole is durable with excellent grip
Suede upper with tonal stitching adds a touch of class
- BrandCalvin Klein
- ModelUlysses Suede
- Weight1.1 pounds
Comfortable and ideal for all-day wear
Long laces ensure easy tying and prevents unraveling
Loosen and break in within a few hours of wear
Run almost 2 sizes larger than standard
Another cheap option that still delivers excellent quality, the London Fog Belmont boasts memory foam sock inner for to ensure comfortable customization and a shoe that remembers you for years. They’re also versatile enough for most weather and keep your feet warm in winter.
Unfortunately, they aren’t as waterproof as we’d like, so check the forecast before heading out. More importantly, though, they’re ideal for a variety of looks and styles and the denim feel is natural without feeling too casual. Our selection of the best cross training shoes offers more great footwear so check it out.
Memory foam sock conforms to the shape of the foot for a customized fit
Suitable for most weather for year-round wearability
Denim feel provides comfort and durability to match with dress pants or jeans
Good quality construction is reliable for daily wear
- BrandLondon Fog
- Weight12 ounces
Lightweight design prevents foot fatigue
Reasonably priced boot for decent quality
Keep your feet warm during winter months
Not as waterproof as we’d like them to be
Arguably the most environmentally friendly chukka boot around, the Timberland Davis Square Leather and Fabric use CORDURA upper construction that’s long lasting and reliable while the Defender Repellent Systems treatment protects from spills, stains, and storms like no other shoe we’ve selected.
It’s on the more casual side of style so it’s perfect for that chill period between spring and summer or summer and fall where you don’t want to lug the heavy boots out just yet. It’s a little difficult to put on and take off, but this should get easier as you break them in. If you love running, our guide to the best zero drop running shoes may interest you.
CORDURA Eco-fabric upper construction
Lace-up closure allows for an adjustable, personalized fit
OrthoLite cushioned footbed provides comfort for all-day wear
Defender Repellent Systems treatment prevents water, oil, and stain damage
- Weight1 pound
50% recycled PET mesh lining is environmentally friendly
Durable design allows for years of wear
Superb snug fit ensures stability on different surfaces
A little too difficult to put on and take off
Highly flexible for maximum mobility, the Cole Haan Grnd Plus Essex Wedgechukka acts much like a hiking boot to ensure your feet stay cool and safe throughout the day. The moisture wicking textile prevents perspiration, and the outsole is perfect for different terrains.
However, it fits a little smaller than standard, so go half a size more than usual at the least. If you can look past this minor issue, though, you’ll discover a shoe that’s lightweight, delivers great energy return, and suits a denim or chinos like few other options. If you like being active, check out our guide to the best hiking shoes.
Highly flexible outsole allows for easy mobility
Moisture wicking textile ensures breathability and keeps feet dry
Outsole designed for excellent traction on different surfaces
Comfortable cushioning suitable for those on their feet all day
- BrandCole Haan
- Weight12.6 ounces
Lightweight construction is easy on the feet and ankles
Pairs well with both chinos and denim for versatile wearing
Superb energy return reduces strain on arch
Fits a little too small than standard
Our final pick of the best chukka boots is the Dr. Martens Sussex 3 Eye which deliver air cushioned soles to absorb shock as you march for whatever the kids are protesting this week to provide the quality comfort you expect from the anti-establishment boot.
It’s also breathable, because not even punks enjoy overheating, and the slip-resistant sole ensures stability. They’re a little too thin for some people, but this is nothing a shoe stretcher can’t fix. Like any decent Dr. Martens, the leather is waterproof and the unmistakable stitching both looks good and ensures they’ll last you until your kids want to take down The Man when you’re too old to do it yourself.
Air cushioned sole with shock absorption properties
Breathable linings allows for comfort when worn all day
Removable contoured EVA footbed with antibacterial treatment
Slip-resistant sole keeps you stable on slippery and uneven surfaces
- BrandDr. Martens
- Weight1.4 pounds
Durable leather construction is waterproof
Long-lasting and vivid stitching design
Easy pull-on heel tab
Boot runs a little thin for some feet
Chukka Boot Buying Guide & FAQ
How We Chose Our Selection Of Chukka Boots
Reviews - Looking at chukka boots reviews was an awesome way of determining which boots are truly the best of the best. They helped us understand the fit, the durability and the comfort, as well as how stylish they looked with a pair of jeans, chinos, or any outfit you want to try.
Price - No one should miss out on great style just because of their budget, so we strove to find as wide of a range of prices as possible. It’s true that cheaper shoes don’t always come with the best durability, but they can at least serve as a stopgap before you look at more expensive options available for your next pair.
Brand - We didn’t want to show too much loyalty to any one brand, and we know different brands offer different qualities and fits. To ensure we found as sufficient of a range of styles as possible, we searched high and low for a variety of brands that all offer something unique to suit whatever style you want to achieve.
Features To Look For In Chukka Boots
Before settling on your favorite pair of desert boots men need in their lives, check out these important features to help determine which option is the right one for you.
Material - The material you choose for your desert boot will depend on the environment you frequent. Those who live in stormy, unpredictable areas will want a boot that’s waterproof, while those who can’t even remember what rain looks like may prefer a more lightweight and breathable shoe.
The flexibility of the boot may vary between materials, though, so also consider your mobility and support when selecting which type of material you want. Some boots also have a combination of materials to provide both waterproofness and breathability.
Laces - The laces of chukka boots are traditionally small to help them maintain the casual, low-profile style. The shortness of these laces can be an issue, as you’re unable to tighten them as much as you’d like, which causes them to unravel. Despite these problems, longer laces can look a little ridiculous, so try to find boots that have a balance.
The laces also come on different materials depending on the brand. Some will have standard cotton laces, whereas others have thicker leather laces that are sturdier and more reliable.
Sole - Even though you won’t wear your chukka boots to scale mountains and hike coast-to-coast trails, the sole is still important for both comfort and grip, especially when wearing them outdoors in the summer. An air cushioned sole provides better comfort and protection, whereas superior tread ensures you won’t slip over should you get caught in wet weather.
Maintenance - How you maintain your chukka boots will depend on which material they are constructed with. Leather is easier to clean, and suede requires a little more care. We do not advise you throw your shoes in the washing machine to clean them.
Instead, you can follow these steps to help keep your boots in the best shape
- Use a shoe tree to help them retain their shape
- Brush occasionally with a soft-bristled brush
- Wipe away clean stains and shiny areas with an eraser
- Stuff with paper to help them dry faster when wet
- Protect the material using water-resistant treatment spray
Best Way To Break-In Chukka Boots
The excitement of buying a new pair of shoes can be quickly doused when you try wearing them for the first time. Most chukka boots take a while to break in, and while some of you may believe you can fight through the pain, most of you will know this is nothing but a losing battle.
To ensure you get the most from your chukka boots and don’t develop a bitterness towards them after they initially scorn you, taking the time to break them in properly will ensure you will feel as good (if not better) than you look when you rock up to the next function oozing style without the pang of a blister in sight.
Slow And Steady
We know it’s tempting to wear your new chukka boots all day, every day, but taking it easy is perhaps the best way to break them in correctly. You can wear them in the morning at a time where the weather is cooler and your feet are better rested before swapping them for an older pair of shoes for the rest of the day before your feet start sweating. You don’t want to be caught shoeless at the office, though, so keep a pair close by for an easy switch.
Ah, Crush It (Crush It Real Good)
A slightly more fun way of breaking your shoes in is to crush, mash, stomp, and throw them around to loosen up the material, just be careful not to cause too much damage to the exterior. Much like you might have ran over your new Converse or Vans to make them look cooler when you were a kid, this makes them more wearable and helps to develop the natural creases that make them more comfortable faster.
If you can’t wait to break them in and need to wear your chukka boots as soon as they arrive, you can at least give yourself some extra protection by investing in thick socks. Not just any old Christmas socks will do, though, so look for those specifically designed for hiking, as they’ll provide the best protection and padding around the heel, and toes which is where blisters most commonly occur.
What’s Around The House?
Maybe getting new socks is too much hassle, though. Maybe all the stores are now closed and you need something to solve your break-in crisis immediately. It’s no good doubling up on pairs of socks, as this can lead to your feet overheating, getting sweaty, and risking the chance of Athlete’s Foot.
Instead, use items you can find around the house to treat your feet and minimize the risk of blisters. You can use cornstarch, which minimizes friction and absorbs sweat, but you can also rub a little petroleum jelly or vaseline onto the area you know a blister will sprout if you’re not careful.
Another option is to get your hands on some blister pads available at any supermarket or shoe store. They work much like band aids but have greater padding to ensure your foot feels fine even if your boots are not broken in completely just yet.
- How to Break In Your New Boots to Prevent Blisters - GQ
- How to Get the Most From Your Shoelaces - Samuel Windsor
- How to Care For Chukka Boots - Our Everyday Life