Though Chelsea boots have existed since the 19th century, they remain a style staple in a contemporary man’s wardrobe. The timeless silhouette and minimalist design allow them to easily assimilate into your current sartorial rotation, whether that means pairing them with a suit during the week or with jeans on the weekend. Their versatile nature lends them to several looks, from casual wear to semi-formal occasions. With that in mind, we’re breaking the best Chelsea boots for men to wear now and in the future.
Best Chelsea Boots for Men at a Glance
Highlights from our list include the following options:
- Best overall: R.M. Williams Comfort Craftsman
- For formal occasions: Our Legacy Camion Boot
- For casual wear: Nicks Heritage Chelsea
- For value for money: Blundstone Men’s Dress
Now you’ve read our favourites, let’s check out the complete list.
1. R.M. Williams Comfort Craftsman
Price: from AUD$649
- Pros: Handcrafted from high-quality yearling leather in Australia, you’ll struggle to find a pair of boots that are perfect for this price. comfortable, practical, durable, etc. the list goes on.
- Cons: While they’re dressy enough for a cocktail dress code, we’d recommend something a little sleeker (Saint Laurent, etc.) if you’re attending balls or other gala events.
If there’s one Chelsea boot to add to your collection, it has and always will be the R.M. Williams Comfort Craftsman. We’re a little biased as this is an icon of Australian fashion, but it’s also a very high-quality boot that comes in at a competitive price point. Handcrafted from a single piece of yearling leather in the brand’s Adelaide workshop, you won’t find another boot that offers this quality for this price.
Once you break them in, they’re comfortable boots, and we have no problem wearing our pair every single day. We’ve selected the Comfort Craftsman because it comes with a rubber welt sole for grip and durability alongside a comfort innersole, but you could also choose a classic pair with a leather outsole if you plan to keep them as dress boots and wear them sparingly. As for the fit, we highly recommend trying these on in-store and getting fitted correctly. They come in three different widths: Narrow, Regular, and Wide, so you’ll want to triple-check everything before you invest in a pair for yourself.
The versatility offered is second to none, and you could just as easily wear these to a dinner party with a cocktail dress code or to your kid’s sports game on the weekend with a pair of denim jeans. Plenty of men also choose a black pair to wear with a suit during the week.
2. Blundstone Men’s Dress
Price: from AUD$239.95
- Pros: Affordable, comfortable, and perfect for casual wear, the Blundstone Men’s Dress is all the boots most people will need. Wear them to the pub for a Sunday roast or the Australian Outback, they’re ready for any adventure you can throw at them.
- Cons: Unlike the R.M. Williams Comfort Craftsman, these boots cannot be repaired. They’re also not handcrafted in Australia, but they’re still very high-quality by all standards. Not a great choice for a formal occasion and we wouldn’t recommend you wear them with a suit.
If you’re looking for a casual, affordable alternative to the R.M. Williams Comfort Craftsman, check out the Blundstone Men’s Dress boot. This Chelsea boot is great for casual and semi-formal occasions where a pair of denim jeans and a button-up shirt is all you need. They’re comfortable, crafted from a soft full-grain leather upper, and double-stitched for durability. More importantly, they come in at an affordable price point of AU$239.95, which is roughly a third of the price of R.M. Williams.
While Blundstone is a privately-owned family company, they don’t make their leather boots in Australia and production is in Vietnam, India, China, Mexico and Thailand. However, we haven’t experienced or heard about any quality issues with their boots since the brand moved production overseas. Of course, a handcrafted pair of R.M. Williams is going to be of higher-quality, and can be restored back to its original condition.
Nevertheless, Blundstone boots have proven themselves to withstand the test of time for their durability, comfort, and style. You’re just as likely to see a pair at your local markets as you are by the campfire in the Australian Outback. Also, check out the brand’s range of gumboots, which are made in Tasmania!
3. Nicks Heritage Chelsea
Price: from AUD$900
- Pros: Custom-made, custom-designed, and comfortable enough to wear every single day. Nick’s boots will outlast you with in-built repairability and durability. As such, we think the high asking price is merely an investment worth making.
- Cons: High price to pay for a boot that’s not particularly suitable for formal occasions and comes across as being a more rugged piece of footwear. You’ll have to measure your foot correctly with a Brannock before purchasing to avoid returns.
If you like the idea of a handcrafted pair of Chelsea boots but don’t want something as dressy as the R.M. Williams Comfort Craftsman, check out Nicks Heritage Chelsea. These are the epitome of custom men’s boots and you can choose everything from the last to the length, width, leather style, toe structure, and outsole. The result is a bespoke pair of boots that offers moderate water resistance, a stiffer more supportive construction that’s great for everyday wear, and a V-bar 700 outsole for comfort and durability.
These are an investment at around $900 plus customisation, but they’re boots that you’ll want to wear every single day after breaking them in. Being hand-made, the elastic, outsole, and nearly everything else is designed to be repaired (R.M. Williams). In fact, maybe the only complaint we’ve ever head about Nick’s boots is the fact they’re so well-made that they can be a little tough to get on and off because of the fit.
In any case, these are perfect for casual and semi-formal occasions and look great with a pair of raw denim jeans and a button-up shirt. We wouldn’t recommend them for your more formal occasions. Also, make sure you measure your foot correctly with a Brannock before purchase. The brand also recommends that you go down half a size from your measurement.
4. Dr Martens 2976 Smooth Chelsea Boots
Price: from AUD$319.99
- Pros: Quintessentially Dr Martens, the 2976 Smooth Chelsea Boots have remained one of the most popular models because of their comfort and quality construction. Suited for casual wear, these are a great everyday boot that will last you a lifetime.
- Cons: Expensive for something that doesn’t use the highest quality leather. The design is a love it or leave it for many.
If the Blundstone Men’s Dress doesn’t catch your fancy, check out the Dr Martens 2976 Smooth Chelsea Boots. Manufactured since the 70s, we’ve had a pair of these in our stable for the better part of 10 years, keeping them on hand for those casual occasions when you want to put together a rugged outfit. They pair perfectly with black denim jeans but also double-knee pants and carpenters. That being said, they’re not a pair of boots we recommend for semi-formal dress codes.
Comfort-wise, they’re perfect for everyday wear with a thick rubber sole, and thanks to the welt stitch across the midsole, they’re also highly durable. Like most boots for men, we’d recommend going down half a size (if possible) to reduce the chance of heel slip. Width-wise, they’re best suited to a regular to wide foot.
This ‘Smooth’ design is our pick of the bunch because of its heritage Smooth leather upper. However, you can also get your hands on a pair of the 2976 Nappa if you want even softer leather that’s slightly less durable.
5. Our Legacy Camion Boot
Price: from AUD$950
- Pros: Stylish, versatile, made from high-quality materials, there’s a lot to like about the Camion. You could wear these with a suit, jeans, cargo pants, and more.
- Cons: The price point is higher than average and has continued to creep upward as the popularity of the boot continues to rise.
Our favourite boot for formal occasions, the Our Legacy Camion Boot not only looks stunning with its perfect silhouette and squared-off toe cap but it’s made with a combination of the highest quality materials you’ll find. In-hand, the vegetable tanned Italian calf leather is buttery soft, while the Vibram outsole (made in the USA) is designed for longevity and durability. There’s attention to detail in the Kilger leather midsole (from Germany) and the YKK side zip closure and metal ‘Our Legacy’ rivet branding on the top of the collar is a nice touch. Our pair is an older model, so it missed out on the metal rivet branding.
Choose from four colours available on the brand’s website: Black, Olive, Deep Sky, and Coney Cognac. We purchased the Olive colour for a semi-formal look, but you could keep it formal and simply choose Black if you want to wear this with a wider range of suit colours.
Fit-wise, check your size with a Brannock and stay true when purchasing. Over time, the boot will wrinkle and age, but that only adds character.
6. Paul Smith Cedric Boot
Price: from AUD$530
- Pros: The sleek design is great for formal occasions, made from high-quality leather in Portugal.
- Cons: While stylish, the design is best suited for formal occasions and doesn’t translate to casual of semi-formal attire particularly well.
With a sharper, formal silhouette, the Paul Smith Black Leather ‘Cedric’ Boots are great dress Chelsea boots. We recommend wearing them during formal occasions and with suits, but you could just as easily throw a pair on with some black denim jeans for a semi-formal look.
As you would expect from a brand like Paul Smith, construction is of the highest quality, and these boots are made in Portugal from 100 per cent leather. They feel great on foot and in hand, and thanks to a lower cut, they’re a little softer around your ankles which aids comfort. The midsole is slightly thinner than the Our Legacy Camion, but it’s about the same as the R.M. Williams Comfort Craftsman so you should expect a similar amount of overall comfort.
They’re also priced a little sharper than designer alternatives, which makes them great value for money, and you can take your pick from a range of different colours, most of which are shapes of brown and tan.
7. KOIO Trento
Price: from AUD$560
- Pros: Made in Tuscany, Italy, with high-quality materials, these are some of the best value-for-money Chelsea boots on our list.
- Cons: Similar to the Paul Smith option, these are not the best for casual wear with a silhouette that’s better suited to formal and semi-formal occasions.
Blending the best of the Our Legacy Camion and the Paul Smith Cedric, the KOIO Trento has a slanted design with a squared-toe cap, which makes it slightly more casual than the Cedric and Ferragamo options.
They’re great value for money, and we find it rather amazing that they’ve managed to produce a handcrafted boot in Tuscany, Italy with LWG Bronze-certified Italian leather at this price. Construction is further enhanced with elasticated side panels for comfort and welted stacked leather outsole which is designed to be re-soled.
We haven’t had a chance to test their water resistance, but the brand states that they have a particularly tight stitch to maximise this aspect of the boot. Finally, there’s a cushioned insole for comfort.
8. Saint Laurent Wyatt Chelsea Boot
Price: from AUD$1,625
- Pros: Supremely stylish and versatile, they might be the most recognisable Chelsea boots in the world. You can wear them with everything from suit pants to skinny jeans.
- Cons: The construction is outstanding, but they’re not twice as good as those boots half the price. You’re paying for the designer name at the end of the day.
Popularised by Kanye West, the Saint Laurent Wyatt Chelsea Boot has been adopted by the most stylish celebrities on the planet, including Harry Styles, Lenny Kravitz, Brooklyn Beckham, Miguel, John Legend, and Justin Bieber. Keep in mind that this is an expensive designer boot and you’ll be halfway to understanding why this boot is so expensive and so popular. It’s made from some of the softest Italian leather we’ve ever touched, but it’s not worlds ahead of the Our Legacy Camion or KOIO Trento we’ve also listed.
Where it stands out is in style and design because not only is it versatile and supremely wearable with a wide variety of outfits from suits to skinny jeans, but people also know what this boot is from a mile away. You’re not wearing Dr Martens, Paul Smith, or KOIO, you’re wearing THOSE Saint Laurent Chelsea boots.
Alternatives to These Chelsea Boots
These are the Chelsea boots we also considered that didn’t make the final cut:
- Astorflex Bitflex Chelsea Boots (from USD$250): Made from healthy, eco-friendly leather, Astorflex offers a collection of stylish, classic shoes, and its Chelsea boots are among the brand’s finest. The ultra-comfortable boots are made using high-end Italian construction for a superior fit.
- Common Projects Chelsea Boots (from AUD$500): Best-known for its low-top minimalist sneakers, Common Projects has branched out recently, offering some of the best Chelsea boots on the market. If you are wondering how to wear Chelsea boots, you can take a sneaker approach with the Common Projects, styling them with jeans for a streetwear vibe. After all, no man’s outfit is complete without the iconic Common Projects embossed lettering on the heel.
- Scarosso Giacomo Nero (from AUD$515): Made in Italy, Scarossa boots combine the old-school shoemaking philosophy with modern design and sustainable practices. The artisanal techniques and luxury materials make the Scarossa Chelsea boots a great option.
If you think there’s a Chelsea boot that we should test for a spot on this list, please contact us via our contact form.
Why You Should Trust Our List
Trust is the backbone of our independent publication, and in curating our list of the best Chelsea boots for men, author Ben McKimm has put a focus on those models that he has first-hand experience with and personally owns in his collection. He’s spent more time and money than he’s willing to admit publicly researching, buying, and wearing boots from this list, including the Our Legacy Camion, Dr Martens 2976, Blundstone, and more recently, a pair of R.M. Williams Comfort Craftsman. In saying that, he’s also leaned on the wider editorial team for their input and experience. Finally, he’s only listed those products that have outstanding materials and represent good value for money.
What is a Chelsea Boot, Anyway?
- HISTORY: Quintessentially English in style, Chelsea boots date back to the Victorian era. They were invented in 1851 by J. Sparkes-Hall, a bootmaker for Queen Victoria, and were worn by both men and women. The boots were originally invented as riding boots, later forming an element of the British mod movement, thanks to them being co-opted by The Beatles during the 1960s.
- TODAY: Chelsea boots are laceless boots designed to slip on and off the foot. Traditionally, they’re comprised of two parts: the vamp and the quarters. Each is constructed from a single piece of leather. The vamp and the quarters meet at the ankle, connected by an elastic or vulcanised rubber gusset extending just below the ankle. These boots typically have rounded toes and low heels and often feature a small heel tab designed to pull the boot on and off easily.
- WHAT MAKES A CHELSEA BOOT: The two main materials used for boots are leather and suede. Leather Chelsea boots are versatile and can be dressed up or down. Their sleek aesthetic works synergistically with the boot’s simple silhouette.
How to Wear Chelsea Boots
If you wondering how to wear Chelsea boots, the black leather version is a refined option that can even be worn with semi-formal and formal outfits in lieu of dress shoes, while the brown leather variety works well with casual, smart casual, and semi-formal looks.
The textured nature of suede imbues a classic boot with a sense of edge, making it an ideal option for casual wear. Black or grey suede shoes suit urban casual looks, while brown suede varieties offer a country vibe. When opting for suede Chelsea boots, ensure you treat your boots with a water-resistant suede protector before wearing them to prevent any weather-related damage.
Casual
Both leather and suede Chelsea boots can be worn for casual looks, though suede gives off a more relaxed vibe. Chelsea boots and jeans make for a chilled, pared-back look; opt for slim-cut jeans over skinny or straight-leg varieties, as this will ensure the hem of your jeans sits nicely over the top of the boot without constricting or drowning it. You can also try cuffing or pin-rolling your jeans to get the most out of your Chelsea boots outfit.
Brown or tan suede boots pair well with distressed denim, while brown or black leather Chelsea boots work well with slim-cut indigo or black denim jeans. Try teaming black Chelsea boots with slim-fitting black jeans and a white t-shirt for a foolproof casual weekend look, or try wearing tan boots with black or faded blue denim, a t-shirt, and a bomber jacket.
Smart Casual
Their sleek, minimalistic silhouette allows Chelsea boots to be worn for smart casual outfits. Both leather and suede boots can be worn in a smart casual outfit. However, black leather is always a safe bet. A pair of black leather Chelsea boots can refine classic outfits like a roll neck or mock neck sweater, black jeans or chinos, and an overcoat.
Grey suede boots also make for an interesting sartorial option; try teaming them with black or charcoal slim-cut chinos, an oxford shirt, a crew neck sweater, and a structured coat. Alternatively, elevate the humble hoodie by pairing it with a structured coat, slim-cut denim or chinos, and a pair of black or dark brown leather Chelsea boots.
Business Casual
Chelsea boots needn’t be relegated to weekend wear; their versatility allows them to be worn throughout the week with business casual outfits. When wearing them to work, opt for a simple black or brown leather silhouette and team your boots with office-appropriate separates, like slim-cut chinos, an oxford shirt or thin roll-neck sweater, and a blazer or structured coat.
Wear black leather Chelsea boots with black chinos, a white Oxford shirt, and a grey blazer. Or, pair brown leather boots with camel chinos, a maroon or rust roll-neck sweater, and a windowpane or checked blazer.
Semi-formal
Their sleek appearance allows Chelsea boots to be incorporated into the modern man’s semi-formal attire. Chelsea boots make an ideal footwear alternative to derby shoes, monk straps, and loafers and can easily be worn with a suit. Like with semi-formal attire, stick to leather varieties. You can even opt for a pair in dark brown or black patent leather to add a sophisticated touch to your Chelsea boots outfit.
For black or grey suits, it’s best to stick with black (potentially patent) leather boots. Navy suits pair well with black or brown boots, while camel or tan suits should be teamed with brown boots. If you’re feeling experimental, you can try styling oxblood Chelsea boots with a camel, dark brown, grey, or charcoal suit.
Your FAQs Answered
Chelsea boots can be worn with jeans, chinos, or suiting separates in slim-cut, tapered varieties.
Trends come and go, but Chelsea boots are a timeless footwear option. These versatile boots are always in style and can be teamed with casual and semi-formal outfits.
Chelsea boots can be worn to work, business meetings, on the weekend, and even to weddings, provided the wedding isn’t black tie.
No, the hem of your jeans or trousers should sit just above or on the top of your boot. If your jeans are too long, you can try pinrolling or cuffing them.
Brown and black Chelsea boots are always versatile options. However, grey suede or oxblood leather also makes for interesting sartorial options.
