LOOKING for a classic boot that will forever stay on-trend? The Chelsea's sleek form and versatility is always a winner.
Often clad in leather—although you'll find just as many great-looking suedes and vegan-crafted versions these days—this slip-on boot is characterised by its close-fitting ankle-high cut, elastic side panels and loop tab at the back which allows you to pull them on effortlessly.
The Chelsea boot originates from the Victorian era and is still going strong today. A solid, dependable choice for adding some polish to your step, the timeless style has been worn by many a well-heeled man: from the 1950s mods of South West London—Chelsea of course, where they get their name from—to contemporary style icons Harry Styles, Paul Mescal and Pharrell Williams.
Despite their classic appeal, there's also plenty of variation when it comes to the style you choose: whether you're after a grunged-up, chunky-soled pair, a cool and casual suede style or something pointy-toed and high shine for maximum impact.
Dressed up or down, there's no denying the versatility of Chelsea boots—and with the winter months still in swing, they're a no-brainer for staying stylish and keeping your feet warm and dry outdoors.
With that in mind, we've pulled together the best Chelsea boots available to buy now, with picks for all budgets. Take a look below.
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1. Best everyday pair: Clarks' Batcombe Top Chelsea Boots
- (AD) Clarks Men's Batcombe Top Chelsea Boots, from £54.41 from Amazon – buy here
You can always rely on Clarks for quality, timeless footwear so they've naturally come up with a solid pair of Chelsea boots here that will see you through the seasons.
With a chunky rubber sole and rounded toe, this brown leather style is ideal for everyday wear as it's not overly formal but still lends a smarter feel to dressed-down attire.
Reviewers are impressed too, with one noting: "Clarks= superb quality and fit." A winning formula we'd say!
2. Best for casual vibes: Grafters' Leather Chelsea Dealer Boots
- (AD) Grafters Leather Chelsea Dealer Boots Air Cushion Soles, £37.99 from Amazon – buy here
Those with a grungier aesthetic will love Grafters' leather chelsea boot: the waxy brown finish creates a vintage, lived-in vibe that's perfect for casual looks.
Crafted from leather, the real standout feature here is the air cushion soles which reviewers say are super-comfortable and ideal for being on your feet all day.
And the good news is—they're also available in black, tan and brown if you're looking for the same shape and comfort but with a bit more polish.
3. Best statement pair: The Kooples' Leather Embellished Chelsea Boots
- ASOS Design Cuban Heel Western Chelsea Boots in Black Faux Leather with Metal Hardware, £35 from Asos – buy here
If you don't mind flamboyant fashion choices then the ASOS Design Cuban Heel Western Chelsea Boots need to be on your radar.
Clad in leather, these boots boast the classic Chelsea silhouette, while the silver-tone toes and cuban heels adds that extra bit of flair.
The swankiest pair of Chelsea boots you might hope to find? We think so.
4. Best vegan approved: New Look's Stone Suedette Chelsea Boots
- Dr. Martens Vegan 2976 Chelsea Boots Cherry, £149 from Office – buy here Look – buy here
Proving that Chelsea boots don't have to look good only in black or brown, Dr.Martens have a deep cherry red boot that's cooler than the rest.
In a shiny finish, these slip-on boots have the classic yellow thread detailing and back pull tab, as well as being set upon a 3cm heel.
For £149, they're an investment that'll look after your feet whatever the weather.
5. Best classic pair: Schuh Black Damien Leather Chelsea Boots
- Schuh Black Damien Leather Chelsea Boots, £58 from Schuh – buy here
Perhaps the most straight-forward and classically-styled of all the options we've listed here are Schuh's Damien Leather Chelsea Boots.
With elastic side panels, rounded toes and pull tabs, this is a boot that sticks to all the traditional features—and does it exceptionally well.
Made from leather, the smooth finish of these boots will look ultra-smart teamed with tailored trousers and a crisp shirt.
6. Best taupe pair: Base London Seymour Chelsea Boots in Taupe Suede
- Base London Seymour Chelsea Boots in Taupe Suede, £75 from Asos – buy here
Base London have been creating their quality shoes since 1995, so naturally the Seymour Chelsea Boots make our list.
Sporting a suede upper in taupe, these boots have a slim sole, classic elasticated insets and a sight heel for some height.
These will go so well with dark denim jeans, whatever the occasion.
7. Best bargain leather pair: REDTAPE Mens Bamford Chelsea Boots Wood
- REDTAPE Mens Bamford Chelsea Boots Wood, £29.99 from Mandmdirect – buy here
On a bit of a tight budget? Don't sleep on the REDTAPE Mens Bamford Chelsea Boots, they're less than £30.
They're even as good quality as some pricier pairs, made from real leather and set upon a man-made sole.
Whether you need a pair for your smart-casual office attire, or for hitting the town on the weekends, these will work just fine for so many outfits.
8. Best street-style pair: River Island Black Transparent Sole Chelsea Boots
- Black Transparent Sole Chelsea Boots, £65 from River Island – buy here
You might recognise the transparent sole of these from the high-fashion runway, but these are actually from high-street favourite River Island.
These leather boots are cheaper than most, yet still good quality enough to last you through years of wear.
Wear yours with an oversized trench and straight-leg jeans for an off-duty, on-trend vibe.
9. Best neutral pair: Mango Leather Chelsea Ankle Boots
- Leather Chelsea Ankle Boots, £89.99 from Mango – buy here
Neutral tones have been trending for a while, so why not add them to your shoe-drobe too with Mango's Leather Chelsea Ankle Boots.
Crafted from 100 percent bovine leather, these ecru boots are part of the brand's committed range, produced using sustainable processes or materials.
And we've never seen a textured sole like that on a Chelsea boot, which makes these stand out as a unique take on the traditional favourite.
10. Best comfy pair: Clarks Desert Chelsea 2 Black Suede
- Desert Chelsea 2 Black Suede, £180 from Clarks – buy here
The Desert Chelsea 2 Black Suedes don't really need an introduction. Everyone knows that Clarks have the comfiest shoes around.
From the cushioned sole to the moulded insole, these hand-crafted boots are sure to keep your feet in check.
The best part? Black boots go with everything. Don't listen to the myth that navy doesn't go with black.
11. Best bargain suede pair: Matalan Grey Suede Chelsea Boots
- Grey Suede Chelsea Boots, £28 from Matalan – buy here
When you're bargain hunting, Matalan should always be your one-stop shop – the Grey Suede Chelsea Boots prove our point.
Available for only £28, these slip-on boots are made from real leather, with all the traditional features of a Chelsea silhouette.
Top style tip: grey and light denim is a Y2K fashion moment.
12. Best winter pair: CC Boulevard Chelsea Boot for Men in Dark Brown
- CC Boulevard Chelsea Boot for Men in Dark Brown, £175 from Timberland – buy here
Timberland basically made big boots trendy, so the CC Boulevard Chelsea Boots are an immediate win.
Made in Portugal with premium Better Leather from a sustainable tannery, these boots have a sturdy, clunky rubber heel.
Think of Timberlands as a lifetime investment. And when they look this good, you'll be yearning for the winter months to come around each year.
How to wear men's Chelsea boots
The beauty of Chelsea boots is just how versatile they are, meaning that you can wear them with chinos or jeans for loads of different occasions.
Yes, they're smart and work for both casual and special events, but there are some definite style must-nots when wearing Chelsea boots…
Our advice to you is to never wear them with shorts or tracksuit bottoms, unless you're chucking something on to run down to the shop. We've all been there.
Should men wear Chelsea boots
Around autumn/winter, when you're walking down the street, wherever you are in the world, you'll probably spot a few pairs of Chelsea boots.
Men have been wearing them ever since they were invented, so of course men can wear Chelsea boots.
We don't believe that fashion is gendered anyway, so men can wear high heels if they wish!
Are Chelsea boots in fashion?
Another benefit of investing in some Chelsea boots is that they are never not in fashion.
This season, we're seeing a lot of clumpy, large heeled gems but generally, the silhouette of a Chelsea boot is always on trend.
Can big men wear Chelsea boots?
If you're on the bigger side size-wise, then all you need to do is opt for some wide-fit Chelsea boots.
There is no reason that larger men shouldn't enjoy the suave edge that they add to an outfit. There are tons of wider styles on the high-street.
Enjoyed our guide for the best Chelsea boots for men? Why not check out the best vegan shoes for men?
We've also rounded up the best boat shoes for men here, to bring some suave Riviera style to your wardrobe this season.
And check out our dedicated Sun Selects fashion section for more style tips, trends and products.
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