Steve Madden Men’s Highline Chelsea Boot
Alpine Men’s Owen Chelsea Boot
Sorel Men’s Ace Chelsea Waterproof Boot
If you are considering an upgrade to your seasonal wardrobe, a new pair of boots is a great place to start, without the need to spend wads of cash on a whole new ensemble. A new pair of men’s leather boots can breath fresh life into both your casual and business outfits and will definitely put a bounce back in your step! Chelsea boots have been around for centuries now and show no signs of ever waning in their popularity. Catapulted to fashion notoriety back in the 1950s and 1960’s, thanks to being found on the feet of rock royalty, this Kings Road London favorite boot, is all about style, comfort, and durability. If it was good enough back then for the Beatles and the Rolling Stones, we’re fairly sure it’s a look that you can carry off today! Of course, choosing your next pair of men’s Chelsea boots is the next step, and you are quite literally spoilt for choice with both classic leather as well as more luxe suede ankle boots on offer. That’s why we’ve pulled together our extensive review of the Best Chelsea Boots around so that you can get off on the right foot! Stay with us as we round up the best leather and suede Chelsea boots for men from a wide range of leading fashion and footwear labels.
The Best Chelsea Boot
If you know your fashion and your footwear, then you’ll know all about Steve Madden. He represents that very rock and roll vibe that the Rolling Stones were all about so it stands to reason that the brand would produce a seriously cool Chelsea Boot. His version is fashioned from weather-beaten suede that gives this boot a more urban edge. Those smart and instantly iconic Chelsea boot elastic inserts make this Steve Madden Highline Chelsea Boot a comfortable, stylish, versatile and effortless ride. It’s undoubtedly a boot that you will get a lot of wear out of. If you need durable boots for your job, check out our guide to the best work boots.
Luxe suede upper in a choice of 5 colors
Matching heel tab and elasticated gores
Comfortable and versatile option
Durable synthetic rubber sole
- BrandSteve Madden
- Weight12 ounces
The Duke from Thursday Company Footwear is designed in that classic Chelsea boot style that you all know and love and is perfect for the modern man. Thursday Company has actually re-designed this favorite style over 20 times to get it just right and to optimize both its style and performance. What they’ve ultimately created is a versatile and elegant men’s leather boot which can be dressed both up or down. Handcrafted with only the finest quality materials, it’s every bit as versatile and dependable as the man who wears it.
Full glove leather lining for ultimate comfort
Extra surface grip studded rubber outsoles
Water resistant and re-soleable Goodyear welt construction
All day comfort thanks to Cork and Poron footbeds
- BrandThursday Boot Company
From GM Golmain this Men’s Chelsea Boot is seriously good value and also comes in a range of colors and additional styles. Hailing from Manhattan, not London in this case, their Chelsea boot is a stylish slip-on in a semi-brogue design. It’s an elegant, practical and straightforward boot constructed from animal-friendly leather to deliver next to skin comfort. With a cushioned insole and TPR sole, the GM Golmain Men’s Chelsea Boot provides durable stability as well as skid resistance. They’re an all-purpose, smart-casual men’s ankle boot.
Soft and breathable animal-friendly leather construction
Memory foam isolate with supportive arc protection
Stable and durable, skid-proof soles
Manufactured using superior handmade techniques
- BrandGM GOLAIMAN
As you would perhaps expect from Timberland, their take on the iconic Chelsea boot is quite utilitarian and robust looking. While these Timberland boots are stylish in its own rugged way, this isn’t a classically elegant leather boot, but it is certainly a handsome and durably constructed one. Constructed with a premium leather upper sourced from a top-rated tannery, the Timberland Logan Bay Chelsea Boot features an anti-fatigue removable footbed. With a convenient twin-gore slip-on entry system, this Timberland is a high performing, comfortable and eco-conscious choice.
Waterproof, insulated and highly durable boot
A comfortable and eco-conscious choice
Features removable anti-fatigue footbed
Made from premium leather and grip stick rubber
- Weight3.59 pounds
We’ve picked out the Sorel Ace Chelsea Boot as our Premium Choice, and as you would expect coming from Sorel, it’s not only stylish and made from premium full grain leather, it’s also waterproof too and features a soft pigskin lining for superior comfort against the skin. The seam-sealed construction keeps the elements out, so your foot stays dry comfortably, as well as looking stylish. These are the perfect premium leather boots to withstand even the heaviest of rain conditions.
Slip-on style with gore panels and back pull tab
Waterproof premium full grain leather upper
Molded rubber midsole with shock absorption
Long-lasting, durable traction
- Weight4.44 pounds
If you fancy yourself as a bit of a city slicker, a real urban cowboy who likes to look sophisticated but with a touch of the outdoors influence about you, then you will love the Keen 59 Chelsea Boot which blends stylish design detailing with solidly dependable full grain leather construction. The overall effect is a handsome but rugged boot with a sturdy rubber sole that provides plenty of support and traction. With a mesh lining, it’s also breathable and the perfect boot for all-day comfort.
Full grain leather upper
Rugged rubber non-marking sole
Breathable mesh-lining for day-long comfort
Lightweight EVA midsole
- Weight1.19 pounds
There’s no need to worry about getting caught out in any rain showers wearing thee Cole Haan Waterproof Chelsea boots. They’re a flawlessly crafted and fashionable leather boot that are just perfect for the rainy season, or any season come to think of it. They make a practical and welcome addition to any discerning man’s wardrobe and have been designed using cutting edge technology to ensure that they are flexible, lightweight and also comfortable. The sole delivers plenty of agility but at the same time stability too for a smooth ride. Make sure you also check our selection of the best Chukka boots for more great footwear.
High quality leather construction
The perfectly polished Chelsea boot
Timeless yet modern style
Flexible, lightweight and supremely comfortable
- BrandCole Haan
- Weight1.44 pounds
Our next product selection comes from Sanitmon and is their men’s Suede Chelsea Boot. It certainly does look very smart and sophisticated in the luxe appeal of suede with three contemporary colors to choose from. The black is super stylish, but we love the grey and light brown options which would look perfect worn respectively with a pair of smart dark denim jeans or a pair of chinos. Santimon specializes in designing and manufacturing traditional boots like the Chelsea, Derby, and Oxford and switch up their materials and designs to match the ever-changing seasons. Their stunning range is suitable for both business as well as casual occasions, and this Chelsea boot is stunning, versatile and comfortable too with its quilted lining.
Luxury suede leather which retains its shape
Soft cork footed and EVA comfort strip for all day long wearability
Moisture-wicking and breathable construction
Three beautiful contemporary and stylish color options
The Owen Chelsea Boot from Alpine is up next, and we picked this one out as our Best Value choice today. The price is sensational, and this is a classic designed Chelsea boot which is bound to become a staple piece of footwear in your wardrobe. With a versatile and timeless silhouette, it’s comfortable to wear and also features a pull on heel tab for easy slip-on. With a faux-faux-leather upper, a lightly padded footbed and non-slip outsole, the Owen Chelsea boot is animal-friendly, comfortable and delivers plenty of reliable traction.
Faux leather upper with stylish contrast stitching
Lightly padded footbed for all day long comfort
Non-slip outsole for reliable traction
Two elastic gore side panels and pull on tab for easy slip-on
- Brandalpine swiss
- ModelBy Alpine Swiss
- Weight3 pounds
The Clarks Bushacre Hill Chelsea Boot is subtle in both color and style and makes an excellent option for both professional as well as more casual occasions. Opt for the rich brown color to go with a multitude of different ensembles with that light brown trim and stitching add just a bit of design detail and color although the other colors in the range are also versatile. Sticking to that classic Chelsea style, this leather ankle boot is flexible, comfortable, breathable and also features a unique non-marking sole that won’t leave scuff marks behind. Find more great boots like this by checking out our guide to the best hunting boots.
Premium leather in a choice of four colors
Stretch gore panels for comfort
Versatile and dependable, classically designed boot
Durable rubber non-marking sole
- Weight12 ounces
Up next we’re taking a look at the Crevo Denham Chelsea Boot which once again, is a versatile and good looking boot which is perfect for either casual or business attire. Constructed out of beautiful and high-quality leather, it’s the kind of kick, just like you, that will only improve with age! This suede Chelsea boot really does wear well and is easy to slip on and off thanks to that tab on the back of the ankle as well as those elasticated heel gores. With a synthetic sole that provides plenty of traction and support, it’s a comfortable, stylish but also cozy Chelsea boot design.
Premium suede in a choice of four colors
Burnished toe Chelsea boot design
Features flexible gore side panels and rear pull tab
Flexible non-slip outer solo
- Weight8 ounces
For a more casual yet still sophisticated pair of Chelsea boots, what about these Stanwell Dockers that are the last word in comfort and easy care? Great for that relaxed off-duty look when paired with jeans, they’re treated with NeverWet technology which, you guessed it, means they will always remain dry and protected and will instantly repel liquids. They all feature Docker’s Comfort Zone technology, so they are extra cushioned and seriously comfy. The durable rubber outsole delivers the look of authentic crepe, but the boot is far more robust and durable and perfect for keeping your feet dry and supported in the wet winter months.
Genuine full grain leather uppers
Treated with revolution wet and stain guard to instantly repel liquids
Feature total comfort technology
Durable rubber outsoles for support and confident grip
- Weight1.38 pounds
While Ugg is undeniably linked to sheepskin and surfer dudes, turns out they do city slicker pretty well too. Their foray into the world of men’s Chelsea boots is undoubtedly worth considering. They created a stylish boot with a leather upper and lining and a good responsive rubber sole. Featuring Treadlite technology, these Ugg Badvin Chelsea Boots really were made for walking and are supremely comfortable, versatile, stylish and easy to wear. With an energy comfort system footbed, you might even be forgiven for thinking that you are wearing a pair of their eponymous sheepskin slippers rather than these rather elegant men’s leather boots. If you need waterproof footwear check out our guide to the best Gore-Tex boots.
Black leather or Chestnut suede construction
Treadlite by UGG rubber outsole
Comfortable and warm lamb leather lining
- Weight1 pounds
Ted Baker is always a popular choice, and these classically styled men’s Chelsea boots are available in your choice of either leather or suede. They’re stylish, practical and super wearable with a printed elastic side gusset and a back tab that’s easy to pull on and off. They deliver the perfect smart casual vibe to any outfit and with that subtly textured heel pattern, elevate this Ted Baker Camrron 4 Chelsea Boot to a whole new stylish and contemporary level. Just check out the detail of the paisley patterned gore side paneling which is a cheeky nod to the company’s Scottish heritage and typical of the Ted Baker quirky style.
Leather upper with elastane gores
Richly colored leather lining with Ted Baker branding
Paisley print embossed on gores
Natural leather sole with rubber heel
- BrandTed Baker
- Weight3 pounds
Manufactured from only the highest quality premium leather imported Cowhide, the Wolverine Montague Chelsea Boots is handsome, rugged and solidly dependable. It’s fashioned and designed in that very classic Chelsea boot style which is known and loved the world over and features a seamless vamp to create an uninterrupted look. This boot easily transitions from casual to formal attire and has a durable and solidly constructed rubber heel and sole.
Quality cowhide leather upper
Natural rubber heel and sole
Seamless vamp for an uninterrupted look
Classic Chelsea design with Wolverine high-quality standards
When it comes to footwear, Kenneth Cole is a bit of a King! Even the brand story itself is one of stellar success in the face of initial financial adversity. We do love good rags to riches story, and we love a fantastic pair of Chelsea boots even more. Our next product recommendation is the Kenneth Cole Reaction Chelsea Boot which is both functional as well as being stylishly fashionable. It might just be the perfect men’s ankle boot. Coming in four classic leather designs which include a suede option, it’s totally wearable and with a memory foam footbed too, is as comfortable to wear as it is elegant to look at.
Low and contemporary ankle height
Available in a choice of Black or Tan leather
Durable rubber sole
Fashionable, functional and comfortable
- BrandKenneth Cole REACTION
- Weight2.2 pounds
If you are looking to upgrade your seasonal footwear and invest in a handsome and solidly reliable pair of gorgeous men’s Chelsea Boots, then these beauties from Gifennse are right up there on the top of our list. They look just stunning and come in either Black or Brown with leather upper, leather lining and a rubber sole. They’re colored using a hand process and are elegant, practical and incredibly versatile. Whether you team them with a sharply tailored two-piece or a pair of crisp chinos, you can effortlessly pull off that smart casual vibe in these Gifennse Chelsea Boots.
Leather upper and leather lining
Sturdily constructed and reliable rubber sole
Manufactured using handmade coloring process
Sleek toe shape adds to the elegant design
You can always trust Calvin Klein to bring a sense of fashion and flair to their footwear, and this Alixander Chelsea Boot certainly does just that. The price is pretty reasonable too, and you have the choice of three colors, all in genuine leather suede. For something a little different, we love the Army Fatigue color which is great for a more casual vibe. They feature double stretch gores and are designed in a lower ankle level bootie style.
Genuine leather suede upper
Double stretch gore for comfort
Stylish and fashionable bootie
Three contemporary color choices
- BrandCalvin Klein
- Weight13 ounces
If sustainable fashion ranks on your list and you like your footwear to be more eco-friendly, then our next choice is a good option for you. It’s the Bitflex Sure Chelsea boot from Astorflex and has been handcrafted in Northern Italy by a company who have been making beautiful boots now for 6 generations. These leather Chelsea boots are the real, premium deal and lovingly made from European leather that’s been softened to form a supply and sumptuous suede. A 100% natural rubber sole completes the boot and provides that perfect symmetry and balance between comfort and style.
Handmade in Italy by a family with 6 generations of experience
Soft, comfortable and already broken in, ready to wear without discomfort
100% natural rubber crepe soles
This richly textured leather Chelsea boot from Aldo is elegant and streamlined and comes in the most sumptuous choice of either Cognac or Black leather. It’s a beautiful example of a traditional men’s leather ankle boot and so versatile and easy to wear. The Chenadien Chelsea boot is snugly designed with side gores for a custom slip-on-fit. There’s also a matching back heel pull-tab.
Manufactured from gorgeous Cognac or Black leather
Classic Chelsea boot with elasticated gore sides
Elegant and traditional styling delivers a versatile boot
Custom slip-on fit
Chelsea Boots Buying Guide & FAQ
How Do We Choose Our Selection Of Chelsea Boots
Our comprehensive product review guides contain a carefully curated and hand-picked cross section of Chelsea boots from a wide range of brands to meet all budgetary requirements. We focus on quality rather than price but of course appreciate that cost can be an important factor in the decision-making process, so our selections try to accommodate low, mid as well as higher price points. We very carefully review and analyze customer feedback and honest consumer appraisals about what they love and loathe about the Chelsea Boots on offer to narrow down our final product recommendations. We aim to include a representative range of brands from the genre, traditional and more contemporary designs as well as various options when it comes to color, material, and construction. If you are ready to upgrade your wardrobe and are seriously considering investing a new pair of men’s Chelsea Boots, then we’re confident the perfect pair for you will be featured in today’s round-up.
Features To Look For In Chelsea Boots
Before you go all guns blazing, diving in to spend your hard earned cash on a pair of shiny new leather or suede shoes, there are a couple of essential features to keep in mind that will help you to make the right decision and not one which you might live to regret. In no particular order, we recommend that you first consider the following.
Material - You are mainly going to have the choice here of either leather or suede or a man-made synthetic option if you are on a budget. Suede does have that more luxurious look and feel and is great for evening wear and also drier weather conditions and environments. If you do opt for suede, then be prepared to carry out some regular maintenance, especially if you are wearing in wet and dirty conditions. Leather is a great all season option and particularly practical in colder and wetter conditions, however, make sure you do invest in sound quality and highly durable leather otherwise you will constantly be having to get your leather ankle boots repaired re-soled and re-healed.
Color - Black is the most popular and traditional color when it comes to men’s footwear generally and is certainly a dependable and versatile choice for a Chelsea boot as it lends itself to so many other outfit colors and styles. From a suit to jeans, and everything else in between, you can’t really go wrong with black. However, if you are experimental with your fashion, already have plenty of black boots and want something more refreshing to uplift your wardrobe or have the budget to purchase multiple pairs, there are plenty of options. Go for brown, burgundy, Elvis’s favorite blue suede, or for one of the increasingly popular exotic animal leathers.
Fit - When it comes to Chelsea Boots, mainly because they don’t have a tight fitting lace system which you can easily adjust, the fit is everything. A Chelsea boot is designed to be close fitting with the flexibility supplied from that side panel so make sure you opt for a pair that fit nice and snug, yes, but that isn’t overly tight. If you go too small and end up with pinched toes and blisters on your ankles, it doesn’t matter how much you paid for your leather boots or how in the fashion they might be, chances are they’ll just get chucked to the back of your wardrobe alongside the other fashion faux-pas you’ve made.
Sole - Of course, pretty much all footwear comes with a sole of some description or other. With a Chelsea boot, your best bet concerning both durability and how it lends itself better stylistically to the overall design aesthetic of this type of men’s footwear is to go for a leather sole.
Comfort - The last word is always reserved for comfort when it comes to footwear! You may well fancy a pair of shiny patent leather, pointed toe boots with a bit of a Cuban heel! Ask yourself through if you really want to try and squeeze your feet into them just because they’re currently all the rage when you know that they are going to cripple you later! A good old fashioned pair of Chelsea boots will always stand the test of time so you can afford to play it safe, keep it simple, opt for something traditional yet still stylish and above all, that slips on comfortably, and you are happy to be seen in and to wear all day long.
The History Of Chelsea Boots
The first iteration of the Chelsea Boot was credited to the shoemaker to the royal court of Queen Victoria and a gentleman by the name of J Sparkes-Hall. Apparently, the Queen was a big fan and was frequently seen out walking in her version of the Chelsea Boot. They are also popularised by horse rider as well as walkers of the time. It wasn’t until an American by the name of Charles Goodyear got his hands on this classic invention that it really began to take shape and form into the famous and recognizable footwear of today. He’s credited with creating the vulcanized rubber process that when into the invention of the elastic gusset and by the 1940s this trend in shoe design was becoming increasingly popular. It enjoyed a further resurgence with the onset of World War One and more recently, in the 1950s and 1960s of what was very much Swinging London, the show of choice for the residents of Chelsea and in particular those frequenting the famous Kings Road. That’s when the name Chelsea stuck and became from thereon in associated with this elasticated side gusset boot.
How To Combine Chelsea Boots
There’s no wrong way really to style your Chelsea Boots. One of the enormous advantages of this fabulous footwear is just how versatile and wearable it really is. Whether you are keeping it classic in black or going for something slightly more contemporary in a quality leather or suede perhaps in a chic burgundy or a tan, they’re the perfect boot to team with everything from a sharply tailored suit, to fitted yet casual chinos with a sports blazer or even with your dark denims. Pick up a dark brown pair, and you can experiment with tweed and other dandy types of fabrics. Don’t be afraid to own and rock your unique individuality. While a Chelsea Boots is a functional, friendly and practical piece of footwear, there’s no need to go all stiff and formal. Streamlined, stylish and straightforward works a treat but if you have the personality to carry off something more outlandish, just go for it. With a boot as forgiving as the Chelsea Boot, you wear them your way.
How To Clean And Care For Your Chelsea Boots
It’s not just cleaning your Chelsea boots which is essential. You need to give them plenty of general TLC if you want to keep them looking in tip-top condition. That’s even more critical if you have opted for a more luxurious but less durable suede pair. Besides wanting them to look good (and clean) you also want your investment to last too, so it pays to take good care of your boots so they can take good care of your feet! We have a couple of top tips to help you out on that score.
- When you are not wearing your boots, it’s a sensible idea to purchase a boot tree to help maintain the integrity of the interior leather and insoles and to keep the boots in their original shape. Don’t just toss your shoes to one side, leave them out on the floor or worse still, store them in plastic bags! If you do, the lack of air might cause them to go moldy
- Unless you are specifically drying out a pair of wet boots by a radiator, don’t be tempted to leave them close to a heat source for any length of time. Too much heat can, unfortunately, cause the leather to warp, crack and go brittle.
- If they’re the kind of boots that you only ever wear in the winter, after which they get stored away, make sure that you give them a thorough clean before you pack them away for an extended period. Take care to remove any salt, chemicals or dirt that would eat away and deteriorate the quality of your boots over time.
- If you’ve gone for a pair of suede Chelsea boots, these both require a different approach to storing and cleaning. They need to be kept in a cool place and not exposed to direct sunlight which can fade the color of the suede. Any humidity and dampness can lead to mildew so make sure that they are clean and dry before you store them. Use a high-quality bristle shoe brush and a specialist suede cleaning product. Don’t use water when you’re cleaning your suede boots as it will damage the texture and surface of the shoes. It’s a good idea to use a suede protective spray after cleaning your suede boots and also before you first wear them to protect them from water damage.
- When it comes specifically to cleaning your leather Chelsea boots, use a soft brush as a harder one might scratch the leather. For any stubborn dirt or debris, you can also use a damp sponge or cloth with a soapy water mixture or even a capful of vinegar. Give them a quick wipe before polishing, or you could buy a specific leather cleaner. Make sure you look after your leather Chelsea boots with pride and regularly polish them. There’s nothing more stylish than a shiny pair of well maintained and cared for boots.
Chelsea Boots FAQ
Q: What are Chelsea Boots?
A: You don’t need to be a dedicated follower of fashion to know what a Chelsea boot is these days. It’s one of those iconic pieces of gentleman’s everyday footwear that has cut through into the mainstream thanks to a host of famous devotees from rock royalty to actual royalty, and no, we don’t mean Kanye West although he is partial to a pair as it goes. Even if you don’t have your finger well and truly on the fashion pulse, it doesn’t take a college degree to guess the origins of the Chelsea Boot. We discussed the history of this elegant and supremely wearable boot earlier, and yes, it does indeed have a foot in the London borough of Chelsea, dating back to Queen Victoria no less.
What we today recognize as the typical Chelsea Boot with its characteristic traits, was down to an American though who patented a process that could vulcanize rubber to create the Chelsea’s boots instantly detectable shape and form. By that, what we are cleverly referring to is that distinctive elasticated side design that all Chelsea Boots must feature and which provides this boot, instead to laces or buckles, with the ease of pulling on and off your foot. Besides that, a Chelsea Boot will be ankle length, typically have a low heel and a round toe and be for the most part principally made from some type of leather. Popularised by the Mods of Great Britain on their scooters, it’s a classic piece of footwear that has always work well with a stylish suit and is as chic today as it was back when Mick Jagger and the Beatles were bowling around town in theirs!
Q: How do Chelsea Boots fit?
A: The Chelsea Boot is designed to be a close-fitting but comfortable ankle boot, hence the elasticated sides panels which enable these boots to be easily pulled on and off. They’ll usually also have a loop or fabric tab on the back which makes donning and doffing even more effortless! Suitable for both men and women, they’re a comfortable fit and ideal for everyday wear. The flexibility of this shoe actually comes from that elasticated side panel rather than from the instep, so it’s essential that you pick the correct fitting pair. We highly recommend you so that my first trying them on rather than just guessing and trusting that the standard size shoe chart will suffice. That’s especially true the higher the price label and the more expensive the leather used in their construction.
Q: What is the difference between Chelsea Boots and Chukka Boots?
A: The Chelsea and the Chukka! Two stylish and popular boots for men but where do they originate from, how are they different and what’s the best way of styling them? We’ve already done some researching into the Chelsea so let’s start with the Chukka which is thought to have derived its name and its style from the game of polo. We’re not sure whether the players wore them on or off their horses, but they became more popular in World War a variation of the Chukka was the chosen footwear for desert-based soldiers. It should come as little surprise then that this boot is commonly also referred to as the desert boot. It’s remained, just like the Chelsea, a favorite boot for men, suitable for both casual and smart occasions.
Regarding how it differentiates from the Chelsea there is one pronounced variation. They may both be ankle boots with a classic plain toe design, but the Chelsea is a slip on whereas the Chukka has eyelets and laces. Generally speaking, you will also find a Chelsea is predominantly made from leather whereas a Chukka is popular in calfskin and suede.
Q: Leather vs. Suede?
A: Generally speaking, leather is used because it tends to be harder wearing as well as easier to take care of, but suede can look really luxe and is excellent in lighter colors for the spring and summer seasons. Leather is durable and versatile and weatherproof too. You can definitely wear leather in far more varying weather conditions than you can a suede boot without fear of damaging it. In either instance, regardless of which material you end up going for, proper maintenance, care, and cleaning program will be required to keep your boots in optimum condition. Leather, of course, needs to be regularly polished whereas with suede, you are going to need a good solid brush and cleaner plus a bit more time dedicated to the pursuit of keeping your new boots in immaculate condition.
- Chukka vs Chelsea – Know your boots this autumn - The British Gent
- How to Wear Chelsea Boots (and What to Look For When You Buy Them) - Complex