Oct' 1911


These Boots Were Made For Walking, The Classic Chukka

As important as it is to maintain versatility and quality on the top part of your body, it’s just as important to look for that same versatility in your footwear, particularly as we transition into the most unpredictable time of year weather wise!  I’ve always been a big fan of boots, particularly for autumn and winter dressing and a firm favourite of mine has long been the desert or chukka boot, a very versatile shoe that will work with almost any trouser and is arguably more comfortable than its Chelsea boot counterpart.  

What is the  difference between a desert and chukka boot you may ask?  All desert boots are chukkas, but not all chukkas are desert boots… chukka boots originally got their name from polo, a chukka is a period of time within the game, similar to a quarter in American football.  Chukkas include two or three eye-holes and are always an ankle-high boot, it’s this structure that makes them a chukka.  Desert boots are a specific subset of chukka boots, they always have crepe rubber soles.   Given this major difference, I’ve always viewed the desert boot as more of a spring time shoe and I prefer a harder, more structured rubber sole for the wetter months.  

Sperry have long been my go-to when it comes to the classic boat shoe (the founder Paul Sperry actually invented the original boat shoe design!) but I’ve only recently discovered their wider range of chukka boots and they’ve fast become one of my most worn boots to date this season.  Using lambskin leather on the inside, they are extremely comfortable, great for commuting and with a hand-stitched outer they are smart enough for almost any occasion.  The chukka design works well with almost any outfit and it’s this versatility that make them a worthy investment for any modern day gent looking to navigate the colder (and wetter months) in stylish fashion.

In a casual cold-weather situation (or even just a time when there’s a bit more chill in the air than normal), a classic turn-up jeans combo works well with the chukka and will allow for all manner of above-waist combinations.  A firm favourite for October has been a funnel-neck knit and suede jacket, with comfort at the forefront without sacrificing on style.

Combine your chukkas with tailored trousers for more office-appropriate vibes or a pair of chinos for a relaxed outfit, more suited to walking the dogs or a Sunday roast by an open fire.  Stay tuned for another chukka inspired post coming next week, featuring more in-depth detail around my three favourite ways to style up this timeless boot.

An enduring style classic for more than half a century, there’s surely no more versatile footwear than a pair of chukkas, a pair of boots sure to become a mainstay in your wardrobe for decades to come.

*This blog feature was written in partnership with Sperry, but as always all thoughts and opinions expressed are very much my own.  Check out the full Gold Cup collection here.*

Get The Look:

Suede Jacket

Funnel-Neck Knit


Sperry Gold Cup Chukka