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The Shoe Styles I've Known of: Chukka Boots

"Pith helmet not included" (Photo from Clarks)

The assertion that all of men’s fashions over the 19th and 20th centuries were derived from either the sporting field or the battlefield could certainly apply to the chukka boot, as the design has made its mark on both. Originally an Indian design, the extremely simple patterning of this boot belies its extraordinary comfort. Hence, its etymology stems from its’ use in the rest period between ‘chukkas’, or periods of play in the popular Colonial pastime of polo.

From these blue-blooded origins, the style made its way to the battlefields of WWII in a form adapted to the desert. This style, typically unlined and utilizing a crepe sole, will not be examined here today, as the longevity and resole-ability of the crepe do not live up to the requirements of a ‘lifetime shoe’. Rather, the more traditional model featuring a stiffer lined upper, plain toe, two or three eyelet facings, and leather or rubber sole, will be recommended.

As with many classic styles, these remain relevant today due to their versatility. The large expanses of leather of the toe and quarters suit textured leathers such as suede, country, or hatch grain, and as such, can work in virtually any casual setting. In mid-brown suede upper and Dainite soles, the default combination for this boot, they can function as a four-season workhorse under jeans, chinos, linen, or wool trousers. With changes to the construction, colour, and sole, they can function as minimally lined summer shoes, or heavy dependable rainy winter walking boots. The ease of maintenance of a suede boot cannot be understated, and they remain perfect weekend footwear for any and all activities.

A chukka boot is also one style where a slightly less expensive model will provide many of the same functional properties as higher-end pairs, and can be a place to economise on the wardrobe. That said, afficionados will always find something special in pairs from the top-tier manufacturers. As with previous articles, shoes will be divided into Attainable (less than 400 USD), Advanced (400-800 USD), and Aspirational (over 800 USD).



At this price point, starting from around 200 USD, you can find good-quality fully leather-lined uppers from established tanneries. These will be built upon a single or double sole featuring leather, rubber, or a combination of both. Goodyear welting is a construction method that should be mandatory in this style. These shoes should cope with a huge amount of wear, and with brushing and shoe tree storage after every wear will last more than three resoles by a reputable cobbler.

Option 1. Meermin 101468 in Snuff Suede

(Photo from Meermin)

Any casual shoe with a suede upper and rubber soles is a potential place to economise in the wardrobe. The differences in quality between shoes in the attainable and aspirational category are far less than with say, a whole-cut oxford. This example from Spanish brand Meermin offers an incredible value proposition.

Made in a brand-owned factory in China, this shoe utilizes a suede upper from Italian Tannery Sciarada. This is Goodyear welted onto a Meermin-branded ‘Dainite-style’ studded rubber sole, which could be re-soled with a genuine Dainite or leather sole.

Other details include full grain lining leather and vegetable tanned insole, built on the modern-round HIRO last, which is described as ‘not too round, but not too elongated’. This last is designed to fit most feet and as such, has a medium-width fore-foot.

One potential caveat for this style is that Meermin shoes have been described as a challenge to break in. These would look fantastic in the shoulder seasons under medium wash jeans, purple socks, a white oxford shirt, and a navy crewneck sweater. A fantastic style for the price.

Option 2. Löf & Tung Cole in Brown Utah calf

(Photo from Skoaktiebolaget)

Löf & Tung have secured a place in the wardrobes of well-dressed men across the world due to their deep understanding of the modern aesthetic and a keen eye for quality. These boots tweak the formula slightly by having uppers made of Utah Calf; an extremely high-quality hatch grain leather from French Tannerie Haas, and more commonly found on shoes by English shoe-making legend Edward Green.

These boots also use genuine Dainite soles, which are Goodyear storm welted onto the soft almond T last in Spain. This last has slightly elongated proportions, but a very standard width and well-clipped heel, which should fit most feet well.

The subtle visual texture of these shoes, combined with the perfect reddish medium brown, makes these shoes extremely versatile year-round. Styling these boots in summer might involve a pair of natural linen-cotton trousers, gold socks, and a denim one-piece collar shirt, and in winter, a pair of medium grey flannels and an ecru submariner’s sweater for a texture-rich ensemble.

Option 3. Loake 1880 Kempton in Brown Suede

(Photo from Loake)

For this classically English style, there is thankfully still one English manufacturer that can provide an option made (at least partially) within the British Isles.

Although unstated on the website, the author has strong suspicions that the upper is made from CF Stead’s Repello suede in a perfect mid-brown shade that can transition perfectly between the seasons and formalities. The Goodyear-welted Dainite sole will provide years of heavy use and several resoles.

The 026 last of this shoe provides a relatively sleek and slightly asymmetrical round toe that suits its’ casual nature. It does have a slightly narrow forefoot, although the soft suede will likely stretch to accommodate all but the widest of feet.

This shoe looks fantastic under a pair of off-white trousers, navy socks, a blue university stripe oxford, and a navy blazer. This marque was recognized for its excellence by a Royal Warrant by Her Majesty the Queen in 2007, solidifying its’ status as a solid and reliable heritage maker.



Although the options in the attainable category already present very viable options, stepping into the next price bracket will provide some material benefits. This may be finer leathers, more refined last shapes, a long prestigious history, or all of the above. Several of the options suggested below offer a slight change of pace in terms of formality and demonstrate the versatility of this style.

Option 1. Alden 1493 Unlined Chukka in Snuff Suede

(Photo from Aden Madison)

For a boot superbly suited to the summer season, you could do far worse than this unlined model from Alden. This model has found many adherents in the #menswear scene due to its’ ability to complement more formal tailored garments while bringing down the overall formality of the look. Another warm-weather feature is the single leather sole which is perfect for dispelling extra heat and body moisture.

Much of the relaxed feel of this boot is due to its' last; the Leydon. This last has a relatively low volume instep and moderate width, with a wider toe box that accommodates most feet. For Alden fans, it is often said to offer a fit midway between the popular Aberdeen and Barrie lasts.

While the loss of the lining leather and rubber sole may slightly affect the boots' longevity, one can be sure that the materials used are the finest available. Resplendent in a bright and warm ‘snuff’ suede, it would suit white jeans, tan socks, and a dark green rugby shirt for a very casual but put-together outfit.

Option 2. TLB Mallorca Artista 133 in Black Boxcalf

(Photo from TLB Mallorca)

The TLB Mallorca Artista range made big waves in the men’s fine footwear community by bringing bespoke details to a comparatively affordable ready-to-wear range. The dynamic and visually arresting last, slim beveled waist and fine-making details of this boot are more commonly found on high-end oxford shoes.

The Goya last used in this model is the culmination of design inspirations from bespoke Japanese craftsmen such as Yohei Fukuda. It features a modern round toe with a tight waist and heel, giving a lovely shape to the out-sole, which is a practical rubber in this case.

The formality of colour and profile of this boot is one of the few examples of a chukka boot that could potentially be worn with a suit. This model would particularly suit a mid-grey sharkskin suit a la Daniel Craig’s James Bond, worn with grey socks, a white shirt, and a black knit tie.

The high shaft of these boots strongly resembles the famous ‘George’ boots worn by British Army Officers in full dress uniforms. Examples of this style of boot can also be found as new or used military surplus from British heritage maker Sanders & Sanders from many online sources.

Option 3. Crockett & Jones Chiltern in Dark Brown Suede

(Photo from Crockett & Jones)

Although the upper leather on this model is similar to other boots introduced thus far, the selectivity that Crockett and Jones' leather specialists employ to choose the hides ensures a flawless upper. This quality control extends to all aspects of the making, with perfectly executed stitching, incredibly comfortable lining leathers, a vegetable tanned insole, mid-sole, and Dainite out-soles.

The fact that Crockett and Jones have been a family-owned company since its’ inception in 1879, and that it employs over 300 people in its Northampton factory and HQ bespeaks of social sustainability that few marques can equal.

This particular boot is built upon the rounded 224 last, which sports a slightly asymmetrical and deeper toe box, with a generous fore-foot that fits most feet well. This particular model looks superb with mid-grey Fresco trousers, forest green socks, and wool, silk, and linen hounds-tooth sport coat in dark tan.



Some may argue that paying upwards of $800 USD for a pair of boots that are inherently utilitarian in nature is folly, but for true devotees, there remain several unique features that may be unattainable at a lower price point. Look for hand-stitching, the finest reverse calf suede, and unique leathers at this price point.

Option 1. Gaziano & Girling Wallis in Polo Suede

(Photo from Gaziano & Girling)

Gaziano Girling requires little introduction. Their Kettering, Northampton-shire manufactured shoes move away from the overly conservative styles of many houses, and the brand has gained notoriety for their very distinctive Deco line.

This boot builds on that unique house style, by increasing the height of the boot shaft and creating a very dynamic profile. The full-grain polo suede uppers are the finest available, and the soles are the practical rubber Wensum units. The 'new-classic' R18 last delivers an elongated round with minimal toe spring for a very Continental look. It may fit slightly narrow feet better than other typical English lasts.

Such visually-dominating boots need a more neutral outfit to anchor them slightly. Perhaps a pair of a mid-grey prince of wales trousers, a navy grenadine tie, a blue oxford shirt, and a navy serge blazer would sufficient to tone down the overall look.

Option 2. Stefano Bemer Chukka Boot in Collare Textured Leather

(Photo from Stefano Bemer)

Another textured leather here, from the late Italian maestro Stefano Bemer. Bemer’s contribution to the bespoke shoe-making world cannot be understated, with his school having trained many of the finest shoemakers of this generation.

While the uppers resemble Kudu leather, one can be assured that no African plains game were harmed in the making of these boots. Rather, the leather has been given a shrunken, vintage leather look by various treatments, which leads to an extremely soft and comfortable upper.

Although relatively restrained in style compared to many of the marque’s other designs, the quality of finishing stands apart from other makers. As already stated, this textured leather works in a variety of circumstances and would suit being worn with a pair of cavalry twill trousers, brown socks, a brown wool tie, and a Harris Tweed jacket.

Option 3. Saint Crispin’s Chukka Boots in Dark Brown Janus calf

(Photo from St. Crispin's)

Transylvanian Saint Crispin’s somehow always manages to produce distinctive and recognizable shoes, despite the current saturation of the footwear market. This is done through unique leathers (particularly colours) and their uniquely Eastern European lasts.

This model has both features, with a ‘bitter chocolate’ upper in C F Stead’s Janus calf suede and a slightly bulbous toe shape of the RIVA last. This last features a narrow waist, almond toe, and sculpted heel. It would be advised to try this boot on prior to purchase.

The rubber soles on this model would suit long winter walks and visits to congenial local pubs. The rounded shaft shape also promotes a comfortable stride, which can be a challenge for some with boots. These would suit being worn with dark wash jeans and a brown shawl collar cardigan in thick Scottish wool.



Chukka boots have always featured in a rounded collection (Photo from Esquire)

As the chukka boot has a history ranging from sport to war and back to kinder times again, it is fitting that this versatility is reflected in its daily wear-ability. A true all-season, all-occasion boot, this model would benefit inclusion in any neophytes’ collection.

Alongside a black cap-toe oxford and all-white classic trainers, a minimal three-shoe collection could cover all bases. From $200 to $1000 USD, a fantastic pair of versatile chukkas awaits…

Disclaimer: Any views represented in this article belong solely to the author and may not represent those of the blog owner. This article is not sponsored by any brands.

Photography: as stated, otherwise own


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