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 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 men's Chelsea boots to buy right now.

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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 dress shoes or casual canvas sneakers, this is an all-rounder shoe that will work with just about any look. This said, it does pay to consider a few small details when styling Chelsea boots.

The most important thing to think about is the colour and construction of your boots. A plain black calfskin leather pair is the safest bet for the office and those more formal occasions. Simply add tailored trousers, a smart Oxford shirt and a blazer for a business-casual look that will take you effortlessly to after-work drinks.

Black boots are easy to wear with almost anything, while other hues like chocolate brown, tan or burgundy present more of a challenge – but don't let that stop you. A brown suede pair of Chelsea boots will work beautifully with denim or corduroy. Try styling them with raw denim jeans, a Merino wool sweater and a corduroy worker jacket for an interesting combination of textures and a contemporary take on classic workwear style.

Patent leather Chelsea boots in a rich burgundy or even bottle green will add a subtle hint of colour to your winter wardrobe. Again, they're easily styled with denim and chunky knitwear, or channel '60s style by opting for a tapered mid-rise flannel trouser and a timeless pea coat.

Best Chelsea boots for men in 2023

Velasca Black Smooth Calf Leather Magut Boots

It doesn't get more classic than this. These men's Chelsea boots from Velasca, made in Italy 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. Perfect for both work and play.

Myrqvist Chocolate Suede Elfvik Boots

Handcrafted in Portugal from the finest hide, these Goodyear-welted suede boots from Stockholm-based footwear label Myrqvist are made to last. The studded rubber sole is particularly ideal for harsher climates.

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.

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 men's Chelsea 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.

Church's Cornwood 3 Soft Grain Leather Chelsea Boot

These chunky commando-soled Chelseas from British heritage brand Church's are deceptively lightweight, offering ultimate all-day comfort. Their casual aesthetic makes them perfect for day to day wear, with chinos or jeans.

Maybe Derby boots are more your vibe?

Shop all men's boots at OPUMO.