There are no fixed rules when it comes to how to wear chukka boots. Street style looks from the fashion capitals of the world have backed a variety of styles, pairing the shoes with anything from designer denim to tailored suits.
Also known as desert boots, the boot was originally designed to be worn by polo players after play – not to be confused with the jodhpur boot, which was worn by players during the match. With a heritage that traverses the military uniforms and street style, there’s no shortage of great chukka boots outfit ideas. Deciding how to wear chukka boots is really just about picking the occasion and letting your sense of style run wild.
Street style influences
Though men's chukka boots have a long heritage and association with institutional looks, coming from polo and the military, their contemporary renaissance is anything but uniform. The look has become a staple of the urban male wardrobe, attested to by its high rotation on the street style scene. A popular styling choice has been to react against the boot’s buttoned-up origins by pairing them with distressed denim and a simple white T-shirt. Denim from Philipp Plein is perfect here, combining great, tailored styles with artful tears and marks of distress.
That said, wearing these men's boots in a slightly less dressed-down context is easy. Simply swap out the distressed denim for dark tailored Levi’s, roll the hem of the jeans to just above the ankle to reveal statement socks for some extra pop, perfect for contexts that require a difficult-to-define ‘smart casual’ outfit.
Classic chukka looks
The emphasis on chukka boots’ street-style credentials shouldn’t suggest that styling them well need be totally removed from the shoe’s origins. 'Chukka' comes from the Hindi word ‘chukkar’ meaning ‘turn’ of ‘circle’, which is also used to describe a spell of play in polo. A great way to style the boot is to recreate aspects of this classic look: pair the boot with trousers and a polo shirt – unsurprisingly, Polo Ralph Lauren is the perfect brand to turn to here. Like the post-match polo outfits that it emulates, it’s a great look that finds a medium between uniformed activewear and casual style.
The name desert boot comes from the chukka’s use in the army as a part of their desert uniform. Though it's rather unlikely anyone is advocating the pairing of men’s desert boots with a full military uniform, why not mine the tradition for looks and pair chukkas with cargo pants or perhaps vintage, ex-military articles? For this look, you’ll need a heavy, sturdy boot to adequately carry the weight of the look – consider shoes from Tod’s for a host of classic styles.
Suited and Chukka Booted
A left-of-field look gaining prominence is to pair men’s chukka boots with a suit. A grey suit is a clever move, as this will resonate well with the brown and tan colours of most chukkas. When choosing your shoes, look to a house like classic English shoemaker Church’s which has a range of chukka boots designed to fit the standards of formality that suits afford. Pairing an unlikely shoe like this one with a suit is a great way to introduce a bit of effervescent informality to the look – perfect for a workplace or event that requires a balance between creativity and formality.
The suit is also a great way to subtly play with textures. The standard desert boot is made in suede, making it quite unlike most shoes worn with a suit. This gives the wearer two options (both equally fun): swap out suede desert boots for straight polished leather, or run with the suede and craft an outfit that meshes materials. Make texturing the theme of the suit by accessorising with a knitted tie and linen pocket square – Italian house Eleventy does both, adapting timeless techniques of Italian tailoring to new and novel accessories. It’s a great way to fully dress-up a suit, but underplay its formality slightly by choosing more informal textures.
Deciding how to wear men’s chukka boots is often about deciding where to wear men’s chukka boots. Equally comfortable in the boardroom or bar, the style is the ultimate in versatile footwear. Invest in a pair you love and enjoy creating a raft of innovative looks around them.