Old Faithfuls: The versatile brilliance of the chukka boot
Old Faithfuls looks at the menswear staples you can always rely on. This month, it’s chukka boots
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There is no shoe that can come close to the chukka boot’s versatility. Sure, loafers can be dressed up or down, worn with a suit or casualwear, but they typically read slightly more formal. Chukka boots, on the other hand, have the ability to span all manner of classic menswear, from looking sharp with a soft Italian suit, to being the perfect finishing touch to a pair of jeans and a T-shirt. Indeed, if you’re looking to invest in just one pair of boots, you’ll likely get the most wear out of chukkas.
Like many great items of clothing, the modern incarnation of these boots began life in the military. British officers favoured the style when stationed in the Egyptian desert during World War II, when they’d have them made in Cairo, basing them on a shoe worn by local traders. These had a soft suede upper and a crepe sole, making them far comfier than the heavy leather boots issued to them. Perhaps more importantly, they caught the eye of Nathan Clark, founder of Clarks’ shoes, who introduced them to Britain upon his return in 1950, dubbing them ‘desert’ boots.
A decade or so later they’d fully caught on, with the Mod subculture in the UK taking a particular liking to them. Early Mods took inspiration from mid-century Italian style, and desert boots worked well with their favoured two- and three-button tailoring. Clarks desert boots also became a key part of Jamaican ‘Rude Boy’ style, while in the US, the soft, casual boots became an instant hit.
Working well as part of a preppy wardrobe, the Ivy League set paired them with chinos, cable knits and tweed, while on film Steve McQueen immortalised the shoes in Bullitt, as well as in his own personal wardrobe. And then there’s James Bond, with Daniel Craig’s stint as 007 seeing him wear versions of chukka and desert boots in all five of the films he starred in. In fact it was Craig, a long-time customer of Crockett & Jones, who introduced the Northampton shoemaker into the Bond universe.
For your own chukka boot adventure, there’s no need to overcomplicate things. A classic two eyelet pair in brown or sand suede will work in virtually any scenario. Chukkas typically look better with a bit of wear too, so treat them like your favourite pair of selvedge jeans and wear them hard, whether on walks at home or cross country road trips abroad.
Timeless chukka boots to buy now
Edward Green Shanklin suede chukka boots
On the more formal end of the chukka spectrum, this pair by Edward Green has been crafted from fine dark brown suede, with a slim, elegant silhouette that would pair best with tailoring for the office, or at a wedding. Made by hand at the brand’s Northampton factory, they come with three eyelets, a sharp rubber sole and a chiseled toe, which the Mods of the ‘60s would surely have appreciated.
Crockett & Jones Molton boots
Crockett & Jones’ Molton style has become a favourite among those looking for boots that work as well dressed up as they do down. They are also a favourite of 007, with Craig wearing them for the Norway scenes in No Time to Die. He picked this very pair, finished in dark brown rough-out suede, a hide developed in collaboration with Ralph Lauren and C&J’s managing director Jonathan Jones. It gives them a waxy, textured look that will become rougher with increased wear, a trait that complements the robust Dainite rubber soles and classic silhouette.
Brunello Cucinelli suede chukka boots
Made by hand in Italy, this pair embodies the relaxed elegance of Brunello Cucinelli, the man and brand behind some of the finest Italian clothing. Like its suits, which are all about softness and comfort, these boots are cut from a soft suede, with a lightly structured upper that will mould to the foot with time. The chunky double sole adds a slightly robust edge, while the light brown colour will work especially well with washed denim and off-white socks.
Clarks Originals Desert boots
The original desert boot, Clarks continues to make the simple two-eyelet ankle boot that its founder first dreamt up in 1950. While no longer made in the UK, the Clarks silhouette remains the most well proportioned of all desert boots, with the simple suede or leather upper perfectly complementing the crepe sole. Available in a range of colours or finishes, we recommend brown or sand suede for versatility. Try them with cuffed jeans and a knitted polo for a Mod-inspired look, or wear with unstructured tailoring to a summer wedding.
Velasca Umbrelèe boots
Another Italian brand taking the chukka seriously, Velasca produces its Umbrelèe model in the Montegranaro region of Italy, calling on the region’s artisans for their craftsmanship skills passed down through the generations. Clearly taking inspiration from Clarks, this pair offers an elevated take on the desert boot, with calf suede, a natural leather lining and a crepe sole with Para rubber extracted from a wild plant found in Parà, Brazil. Designed for comfort as well as style, try them with tailored trousers, an Oxford shirt and a field jacket.
