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Chukka boots are the “it” shoes for men today. They are stylish and durable footwear for any outfit, which explains why their popularity has exploded in recent years. These boots have a timeless, classic style. Even the Duke of Windsor was rocking a pair of Chukka boots back in 1924. That lead to increased demand by the 1940s.
They are available in a variety of quality materials, which can make it hard to choose the best Chukka boots for your style. That’s why I put this guide together for you. I want to help you understand what the Chukka boot is, how it is made, and even how to wear them. There are also valuable reviews on specific Chukka boot styles.
There is some debate over how Chukka boots got their name. Many say it came from a period in the game of Polo known as a Chukka or Chukker. Others believe it has a Hindi origin. Then some feel the name connects to its resemblance to the Polo boot the Jodhpur. The Indian word Chukkar has also gotten mentioned as a possible origin.
It is a common misconception that Chukkas got worn during Polo matches. Players of the game often wore the boots, but it was after their competition and not during gameplay.
A version of the Chukka boot got worn by British soldiers during WWII. They had crepe rubber soles and not the traditional leather soles. That was to provide better traction for the soldiers in the terrain. Those boots were known as desert boots. Talk about some stylish soldiers!
Chukkas became mainstream footwear for men in the 1940s and 1950s. Men loved the comfort of the boot and its versatility to be worn casual or formal.
Eventually, they reached Hollywood. Over the years, celebrities have been worn chukkas in varying styles like Marlon Brando, Steve McQueen, Zac Efron, and the always dapper David Beckham (I’m sure Posh Spice approves).
What Makes it a Chukka Boot
All Chukka boots have unique features that distinguish them as the genuine article. Other boots claim to be Chukkas, but if they don’t follow my list below, they are posers. Use this as a guide when shopping for your Chukka boots.
- A true Chukka is always ankle-high.
- It has two or three eyelets. No more, no less.
- Chukkas are a lace-up boot.
- There is a rounded toe box on every Chukka.
- Traditionally they have suede uppers made from calf leather.
- They get constructed in two parts, the quarters and the vamp.
- A thin leather sole is most common, but a rubber outsole is available for a more casual style.
If you want to get a more rugged boot, opt for the crepe sole. For more elegant usage, choose the thin leather sole.
Formal or Casual: What to Look for When Buying
Some Chukkas can get used in casual or formal style applications, while others are strictly casual.
Rubber sole (crepe sole) versions always get worn casually. It is best to wear them with jeans or khaki pants. You don’t want to wear them with a suit or dress pants because they do not go together.
Leather soled Chukkas with contrasting stitching is also considered a casual boot. Because of the different colors, they should never get worn with dress pants or suits.
Thin leather-soled boots in a dark brown or tan colors are the most versatile type. They can be dressed up or dressed down depending on the season, event, or your signature style. You can pair these with a suit, Chinos, dress pants, khakis, jeans, or even shorts.
In my opinion, the best Chukka boots for men are the classic brown suede boots with a thin leather sole. These are unquestionably my favorite type of Chukkas. They are the ones that I wear most often. Choosing those gives you the ability to wear them year-round, with virtually any outfit. Not to mention how much easier it is to put your outfits together in the mornings.
Styling Your Chukkas with Your Wardrobe
How to wear your Chukka boots depends on the boot style you have. I’ve put together some wardrobe pairings to help you combine your pieces.
Black leather Chukkas have a sleek appearance and go with most outfits. Try wearing them with these:
- Black leather jacket
- Chinos and a sweater
- Slacks and a sportcoat
- Camel coat
- Suit
Brown Chukkas match with many things and are well suited for the fall and winter months. Check out these pairings:
- Sweater and dress pants
- Business casual jeans and a button-down shirt
- A utility jacket with jeans
- Tan chinos with a light blue dress shirt
- Gray suit with a collared shirt and a dark tie
Comparison Table
Product
Material
Price
The 10 Best Chukka Boots for Men in 2022
1. Clarks Men's Bushacre 2 Chukka Boot
FEATURES
- Multiple color options
- Cushioned insoles
- Rubber outsoles
- Available in leather or suede
This pair is available in 100% waxy leather or suede. There are numerous colors to choose from, like dark brown, black, wheat, navy, and rust. It has two eyelets for laces and a cushioned insole with rubber outsoles.
Some people have experienced problems with the leather upper becoming separated from the outsole of the boot. That is said to happen after a few months of normal wear.
PROS
- Great value for the cost
- Flawless appearance
- Versatile
CONS
- Sizes run a bit large
- Rubber sole sometimes squeaks
- Casual style only
2. Timberland Men's EK Brook Park Chukka Boot
FEATURES
- Premium leather uppers
- Three color options
- Pull-on loop
- Leather heel welt
- Gripstick™ rubber outsoles (made with 34% recycled rubber)
- Linings are made with 50% PET (recycled plastic bottles)
- Anti-fatigue comfort technology
This leather Chukka has two eyelets, contrast stitching, and 100% leather. It also has a loop on the back to assist in pulling it on. This fashion brand uses its comfort technology to give you support and comfort the whole day.
The soles on these are unique. They use a special blend of rubber known as Gripstick™; to provide you with the toughest traction possible. If you’re looking for a durable boot for more rugged wear, this is a good pick. Remember, this pair is strictly for casual wear.
PROS
- Sleek lines
- Premium materials
- Comfort guaranteed
- Durable
CONS
- The pull-on loop takes away from the boot's aesthetic
3. Thursday Boot Company Scout Men's Chukka Boot
FEATURES
- Shock absorption
- Antimicrobial footbed
- Studded rubber outsoles
- Available in leather or suede
- Cork-bed mid-soles
- Supple interior
- Waterproof
You can get this snazzy boot in brown leather or suede upper with cognac and dark olive shades. It has a studded rubber outsole with sturdy construction and extra grip power.
This brand strives for durability and uses only top quality leather. It has luxury features like a supple leather interior, antimicrobial footbed, shock absorption, and cork-bed mid-soles. As a bonus, this boot is waterproof!
Sizing on these has been debatable, with the company recommending you order a half size down and customer reviews adamantly against it.
PROS
- The Cadillac of boots
- Waterproof Chukka
- High comfort level
- Elegant
CONS
- Sometimes bulky and stiff
4. UGG Men's Neumel Boot
FEATURES
- UGGpure™ wool insole and lining
- Rubber outsoles
- Suede uppers
- Slipper option
No doubt, this is the coziest Chukka on the list. It has the same basic design as other styles with a leather upper, rubber outsole, and three eyelets.
What makes this boot stand out from other brands is its signature UGGpure™ wool insole and lining. Just looking at the picture makes you want to snuggle up inside a pair and read a good book.
They are a casual winter boot and should get worn with jeans and a sweater or other cold-weather casual attire.
PROS
- Extremely cozy
- Additional warmth for winter months
- Insole and lining unique to this brand
- Can be worn as a slipper
CONS
- Winter boot only
- Casual style only
- Limited styling options
5. Dr. Martens Men's Cabrillo
FEATURES
- Contrast stitching
- Rubber outsoles
- Leather uppers
- Doc Martens AirWair technology
The most casual boot style on my list so far, these Doc Martens feature the brands easily identifiable yellow contrast stitching, grooved edges, and a logo tab on the heel. They are available in colors like Gaucho Crazy Horse, Acorn, and Black Wyoming.
They’ve got the Chukka boot rubber sole, leather upper, and two eyelets. The air-cushioned insole is the popular Doc Martens AirWair technology.
This boot is designed for daily wear and come looking already broken in. You can wear this style with jeans and a t-shirt.
PROS
- Comfortable insole
- Doc Martens reputation for quality
- Well known designer
CONS
- Casual style only
- Limited styling options
6. Red Wing Heritage Men's Weekender Chukka Boot
FEATURES
- ComfortForce footbed
- Flexible rubber outsoles
- S. B. Tanning Company leather uppers
- Multiple color options
- Stitched down construction
The designer of this boot is the highly respected Red Wing company. Known for their stitched down boot construction, they make an incredibly durable pair of Chukka boots.
The Weekender features a flexible rubber sole and a ComfortForce footbed. S.B. Tanning Company is the leather supplier for the uppers. These are a lightweight option if you don’t like the clunky feel of some boots.
You can expect superior craftsmanship in this style exclusively made in the USA. They are available in six colors: Copper Rough & Tough, Hawthorne Muleskinner, Red Maple, Concrete Rough & Tough, Bourbon Yuma, and Red Maple Muleskinner.
PROS
- Flexible and lightweight
- Multiple color options
- Well-constructed
- Made in the USA
CONS
- Mid-range price point
- Casual style only
7. Cole Haan Men's Glenn Chukka Boot
FEATURES
- 100% Leather
- Leather outsoles
- Stacked heel
- Multiple color options
- Multiple textures
I like the upper color choices. In leather, the colors are Java, Camello, Black, and Dark Full Grey. Suede offers the Milkshake, Folkestone, and Moon Chip shades.
The Camello has a slick, smooth finish. All other leather uppers have a textured appearance. I suspect they are constructed with full-grain leather, but could not confirm it.
The Milkshake would be my boot of choice. That color, combined with the thin leather sole, makes it the most versatile selection. Great for year-round use for casual and formal occasions.
PROS
- Color selection
- Different leather finishes
- Leather soles
- Soft leather
- Styling flexibility
- High comfort ratings
CONS
- Mid-range price point
- Slippery when wet
8. Frye Men's Bowery Chukka Boot
FEATURES
- Oiled suede
- Multiple color options
- Leather and rubber outsoles
- Improved grip
Merge alert! Frye has created one of the most incomparable boots on my list. Of course, it has the traditional Chukka leather or suede top with a handful of color selections. But when it comes to the sole, they’ve thrown down the gauntlet. This boot features a leather sole and a rubber sole! Yes, both materials on one boot! I’m shook.
To improve grip and provide additional comfort, it has the classic leather sole with a rubber sole on the forepart (bottom). It’s like getting the best of both worlds.
PROS
- Unique design
- Formal or casual styling
- Durable construction
CONS
- Less formal than an all leather sole
- Can get pricey
9. Allen Edmonds Men's Cyrus Chukka Boot
FEATURES
- Premium European suede and calfskin leather
- Two color options
- Comfortable ShockForm™ insole cushion
- Leather outsoles
Allen Edmonds is renowned for making top-quality shoes with the finest materials. This boot has leather soles with a Shock Form Insole along with Black Milled Lining.
I dislike this particular boot, strictly because of the messy heel aesthetics. The black leather option is slightly less unlikable with one color. However, the tan suede is undesirable with its different colors and textures. The loops, straps, and heel reinforcement ruin the timeless look of a Chukka boot. But that’s just my opinion.
PROS
- Dress-casual chukka boot with an unique design
- Leather soles
- Made in the USA
CONS
- Not a classic chukka design
- Pricey
10. Tod's Men Desert Boots Testa di Moro
FEATURES
- Suede uppers
- Rubber outsoles
Available in only one color, Testa Di Moro, this is one of the higher-priced styles you can get. They get produced in Italy with a suede upper and rubber sole with traction grips.
There is a faint “T” embossed on the boot just below the bottom eyelet. It’s nice they didn’t make a large logo. Unfortunately, it’s visible enough that it looks like a stain on the boot.
PROS
- Italian design
- Classic dark brown color
- Stylish and elegant
CONS
- Logo placement
- Pricey
Frequently Asked Questions
Chukka Boots vs. Desert Boots: What's the Difference?
Desert boots are a subcategory of Chukka boots. That means all desert boots are considered Chukka boots, however not all Chukka boots can be called desert boots. Both feature the same basic style, two or three eyelets, and two-piece uppers.
The defining difference between desert boots and Chukkas are material. The classic desert boot gets constructed of a light suede upper, although sometimes available in leather today, but always with a crepe rubber sole.
Crepe soles give the desert boot a textured bottom with a gummy feel. It is a heavy flexible material designed for desert soldiers in WWII.
How Do I Lace My Chukka Boots?
The way you lace your boots depends on your preferences, the occasion you’re dressing for, and the type of look you want to achieve, be it casual or formal.
For a casual look or event, it is acceptable to use the standard cross-lacing method with a bow tied on the top outside portion of the boot. That is also known as everyday lacing.
Special occasions and formal events call for the elegant straight-bar lacing technique. That gives the boot a sleek, streamlined appearance that is classy and clean.
Are Chukka Boots Business Casual?
Yes, but not exclusively. One of the best features of Chukka boots is their ability to transition from formal to casual effortlessly. The right pair of Chukkas can get worn for any occasion, and most are great for casual through business casual.
If you style your Chukkas well, you can pull off almost any look. For business casual, I recommend a dark-colored boot paired with chinos or dress pants, a button-down shirt, and a sweater or sport coat. You will fit right in at the office.
I'm in College. Which Chukkas Have a Young Vibe?
I know just the pair for you! The designer Cole Haan has the GrandPro Rally Chukka Sneaker. It is an exclusive design that flawlessly merges the classic Chukka with modern-day tennis shoes.
In true Chukka style, they have leather uppers, three eyelets, and rubber soles. They are a very polished boot with a youthful glow about them.
I highly recommend these boots if you want to look fly while having fun. Those are the best of both worlds.
Final Thoughts!
With a long history and ties to everything from Polo, to the military, to the Royal Family, Chukkas are one fashion icon that’s here to stay. Having options like calfskin, half-grain leather, suede, full-grain leather, and a waterproof Chukka, there’s going to be the right boot for you.
Chukka boots are a staple piece for every man’s wardrobe. Dress them up, or dress them down. These boots are adaptable for any outfit and all seasons.
I hope you found the information in this buyer’s guide useful. Let me know if I helped you find the best Chukka boots for you by commenting below!
