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20 Best Men’s Chelsea Boots To Wear In 2023

Looking for the best men's Chelsea boots? You're in the right place.

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If you haven’t heard of the legendary men’s Chelsea boot then your wardrobe has been missing out on one of the most reliable and stylish footwear options for men today.

What makes the humble Chelsea boot so popular? Predominantly, its ability to seamlessly transition between both the casual and formal wardrobe. Men’s Chelsea boots can be worn with a suit just as well as a pair of jeans, with the only rule being that they should be well looked after to retain their polished appeal.

With an illustrious ancestry extending back to the British monarchy, the Chelsea boot design was conceived by J. Sparks-Hall, Queen Victoria’s personal shoemaker. Chelsea boots (which wasn’t named as such in the early days) proved popular with horse riders due to their durable nature and lack of laces to risk getting tangled.

A quick walk down memory lane shows that Chelsea boots for men were originally intended as riding boots, but the little band you may have heard of, The Beatles, would eventually wear them on stage – as well as The Rolling Stones – launching them into the menswear essentials lookbook until the end of time.

But what should you look out for when searching for the best men’s Chelsea boots?

Men’s Chelsea Boot Materials

The majority of Chelsea boots for men are going to be made from either leather or suede, with each material being better suited to winter and summer, respectively. Leather not only provides better protection against the winter elements of rain and snow, but it also moulds to your foot over time, making them more and more comfortable with each wear.

Suede, due to it being slightly harder to clean, is better suited to being worn in the summer months where they’re going to be less at risk of stains and rain. You’re more likely to find suede Chelsea boots in a wider range of colours too, so plenty of space for showing off your true colours.

Chelsea Boot Styles

As with any boot, men’s Chelsea boots can be styled in various ways. You can find Chelsea boots that end at the ankle, or finish above it. The higher the fit the easier the Chelsea boots are to wear with a suit as the top can be covered by your pants. Lower-fitting styles will end up showing more skin when you sit down, and nobody really wants that.

The style of the toe can differ from pair to pair too. Rounded toes are the perfect all-rounder, meaning they can be worn up or down, depending on the situation you find yourself in. Pointed toes are a harder style to pull off, and you’ll likely see these on the feet of mod-rockers and the more ‘rebellious’ types. Of course, they also lend well to more formal occasions.

Chelsea Boot Last

When searching for a pair of men’s Chelsea boots, you’re likely going to come across the term ‘last’, particularly with pairs from the more high-end manufacturers. A last is a solid form around which the boot is moulded. You’ll see a number associated with a particular last, and this could be exclusive to a particular brand, your knowledge of a brand will come good here. Although, if you’re not entirely sure what each last means for each manufacturer, a visit to a store or a quick email will help you out.

With the resurgence of the Chelsea boot in the men’s fashion space, there’s no shortage of materials, colours and price points to choose from. Thankfully we’re about to make your job easier with a selection of the best Chelsea boots for men to buy right now. And once you’ve done that you can learn how to wear and style them.

Our selection of Chelsea boots…