It's widely acknowledged that the Chelsea boot is one of the most versatile shoe styles out there. Occupying the territory between smart and casual, it's the perfect all occasion boot and thus a fail-safe investment that will prove its worth time and again. Here, we've compiled an ultimate guide to Chelsea boots, in which we detail everything from their rich history to how to wear them and the styles on our radar at the moment.
The Chelsea boot was first popularised in the mid-19th century, when Queen Victoria's shoemaker created a pair of ankle boots with elastic inserts either side, to make it easier for the queen to pull them on and off. Soon, the boot became known as the 'paddock boot' and was adopted by equestrians and country folk, who favoured it for its sturdiness and practicality.
By the 1950s and '60s, paddock boots had gained popularity in Swinging London and were adopted as the footwear of choice by the fashionable Chelsea set – hence their new name, Chelsea boots. All the A-listers at the time – from The Rolling Stones and The Beatles to Jean Shrimpton and Mary Quant – were regularly seen sporting Chelsea boots on the streets of London, cementing them as a paragon of effortlessly cool style.
Today, Chelsea boots endure as a footwear staple beloved by everyone from farmers to high profile celebrities. Comfortable and practical yet eternally stylish, they're not set to go out of style anytime soon.
The best thing about the Chelsea boot is its inherent versatility. Unlike formal Oxford shoes or casual canvas sneakers, this is an all-rounder shoe that will work with just about any look. Dress them up with tailored trousers, a smart Oxford shirt and a blazer for those more formal occasions, or opt for a workwear aesthetic with an overshirt and corduroy trousers. For an easy weekend look, team your Chelsea boots with your go-to pair of denim jeans, a cashmere sweater and a timeless pea coat.
Handcrafted in Portugal from the finest suede, these Goodyear welted boots from Myrqvist are made to last. The studded rubber sole is particularly ideal for harsher climates.
Hardgraft's commitment to the highest quality craftsmanship is made evident in this black boot sneaker hybrid. Hand-built crepe soles offer the lightweight comfort of a sneaker while sock-like suede uppers act like gloves on your feet.
This style from Duke + Dexter offers a novel take on the classic Chelsea boot. The rubberised crepe sole provides ultimate comfort and durability, while a slightly worn effect creates a lived-in look that will work just as well with jeans and a tee as with more formal wear.
It doesn't get more classic than this. These boots from Velasca, made from full-grain leather with a durable Vibram rubber sole, are a timeless addition to any outfit that you'll reach for time and again.
The commando profile of these full grain nappa leather boots from ETQ Amsterdam lends them a military-style aesthetic, making them perfect for subtly toughening up any outfit.
For a more contemporary take on the traditional Chelsea boot style, you can't go past these beautifully made suede truffle-coloured boots from Oliver Cabell. They'll look great with a trusty mac coat on your winter walks.
Swedish label Axel Arigato may be known for its streetwear-inspired sneaker designs, but its first foray into bootmaking is an obvious success. These premium suede boots come with a removable moulded insole that's designed to mimic the comfort of sneakers.
Shop all men's boots at OPUMO.
Shop all men's footwear at OPUMO.
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