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 our pick of the best Chelsea boots to buy right now.

A brief history of the Chelsea boot

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.

How to wear Chelsea boots

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.

10 of the best Chelsea boots for men

Velasca Black Smooth Calf Leather Magut Boots

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.

Myrqvist Chocolate Suede Elfvik Boots

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 Off Black Chelsea Boots

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.

ETQ Amsterdam Black CB 01 Boots

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.

Oliver Cabell Lion Chelsea Boot

For a more contemporary take on the traditional Chelsea boot style, you can't go past these beautifully made suede beige-coloured boots from Oliver Cabell. They'll look great with a trusty mac coat on your winter walks.

Axel Arigato Brown Chelsea Boots

Swedish label Axel Arigato may be best-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.

KLEMAN Tonnant VGT Boots

The Tonnant VGT Chelsea Boot is part of KLEMAN's eco-responsible collection, which only uses leather that has been tanned without the use of any chromium salts or heavy metals. Crafted in France from rich Italian vegetable-tanned leather and boasting a sturdy rubber sole, these boots are made to last.

Aurélien Brown City Chelsea Boots

Handcrafted using the finest oiled suede from the most respected British tannery, these sleek Aurélien boots epitomise the brand's commitment to top notch craftsmanship. The extra padded insole and durable rubber outsole lend them all-day comfort, ensuring you'll reach for them time and again.

Royal RepubliQ Collision Chelsea Boots

These thick-soled Chelsea boots from Dutch footwear label Royal RepubliQ bring classic Teddy Boy style into the 21st century. Made from 100% leather with a unique two-tone effect called “abrasivato", they'll inject your outfit with the perfect amount of attitude.

Shop all men's boots at OPUMO.

Shop all men's footwear at OPUMO.