Around for over 150 years and best associated with The Beatles, Chelsea boots are an excellent shoe that have a place in the wardrobes of men and women alike. Much like the best chukka boots, the best Chelsea boots are a versatile footwear choice for a plethora of occasions from casual to formal and everywhere in between.
Whether they’re crafted using the finest bespoke leather or from classic suede for warmer climates, they can match with dress pants, jeans, khakis, chinos, and you might even see some brave souls sporting them with shorts.
If you’ve not got a pair of Chelsea boots on your shoe rack, it’s time to change that.
The Best Chelsea Boot
The iconic Dr. Martens 2967 are, for many, the only Chelsea boot to consider. It boasts the classic style with the famously Doc Martens edge that’s rocked by both men and women alike.
The elastic stretch means they’re easy to pull on, which is helped by the logoed pull loop you can find at the heel. For all day wear, the signature bouncing sole will protect your feet, while still offering ample room for thicker socks during winter. They’re a little heavy, but you’ll get used to that in no time. If you have issues breaking into your new boots, check our our guide to the best shoe stretchers.
Woven stretch goring inserts
Logoed pull-on loop at heel
Signature bouncing sole
Wide boot opening for easy wear
- BrandDr. Martens
- Model2976 Chelsea Boot-U
- Weight3.7 pounds
Stylish boot for men and women
Ample room to wear thicker socks in cold weather
Comfortable and durable design and construction
Weight takes some getting used to
The Bruno Marc Philly Dress provide superb support at a superb price. The latex sole delivers a solid tread for slippery surfaces and saves you falling over, while the rounded toe is suitable for both formal and informal occasions and events.
Again, they’ll suit men just as much as they’ll suit women, and the synthetic leather errs on the cruelty-free side of shoe materials and gives it essential flexibility. However, they run a size too large, so be wary of this when buying. To keep these boots always as good as new check out our guide to the best shoe protection sprays.
Ankle boot design offers support
Latex sole with solid tread
Fabric insole for consistent all-day comfort
Rounded toe suited to variety of occasions
- BrandBruno Marc
- Weight1 pound
Suitable for both men and women
Flexible synthetic leather provides greater mobility
Plenty of room in the instep
Size runs a size too large
With the unmistakable embossed logo, the Clarks Bushacre Hill is sure to catch the eye of the fashion-forward readers among you. Like any decent Chelsea boot, they provide easy removal while also boasting waterproofness for wet weather.
Inside, the textile linings prevent rubbing and irritation, keeping you comfortable when matching them with whatever pants you like for any occasion. The top of the boot may dig into your shins at first, but this should ease once you’ve broken them in. Make sure you also check our guide to the best hiking shoes.
Stretch gore panels for easy removal
Premium leather construction is waterproof and durable
Durable rubber outsole ensure comfortable fit
Smooth textile linings prevent rubbing and irritation
- Weight12 ounces
Matches well with chinos, khakis, or jeans
Designed to look worn and rugged for the perfect style
Snug fit while still leaving a little wiggle room for toes
Top of the boot may dig into shins
With a tough heel loop and suede construction, the Steve Madden Highline are a great outdoor Chelsea boot for those who like their shoes rough and ready. The true to size fit helps your foot slide seamlessly inside, and the upper is flexible to accommodate a variety of inclines, declines, twists, and turns.
The soles might squeak on wooden floors, so maybe warn others about that. But if your office is carpeted, you can invest in these for a great pair of work boots that look great with a pair of smart dark jeans or chinos. Our handy guide to the best running shoes for beginners features more great products like this.
Heel loop for easy wear and take off
Sophisticated stitching adds extra flair
Supple upper is flexible
Suede construction is long-lasting and durable
- BrandSteve Madden
- Weight12 ounces
Look great with dark jeans for the office
Suitable for winter weather (with protective spray)
Comfortable fit that’s true to size
Soles may squeak on wooden floors
Boasting high-quality design and construction, there’s a lot to love about the Calvin Klein Larry. The comfortable insole ensure easy all-day wear, while the variety of color options means there’s an elegant style for everybody.
It’s suitable for both casual and formal occasions, but you might need to pull the hoe stretcher out to fix the narrow center. If you’ve got thinner feet, though, this sleek, hip shoe will take you right back to your stylish teen years and prove to your kids you’re the coolest cat in town.
Quality construction built to last
Easy to slip on and take off
Comfortable insole for all-day wear
Elegant design with multiple color options
- BrandCalvin Klein
- Weight12 ounces
Suitable for both formal and casual occasions
Sleek and hip style perfect for the younger crowd
Great price without sacrificing quality
Runs narrow down center of foot
The Kenneth Cole Reaction Suede provides comfort and support and is an excellent choice for those blessed (or not so blessed) with wider feet. It has a wide foot opening that complements the wide elastic panels making it easy to put on and take off, while the removable insole also allows for extra room or orthopedic inserts.
You may need these, too, as it’s quite lacking in arch support compared, which is a disappointment considering the price. This depends on your foot shape, though, and if you’re looking for style and quality (and a way to keep your feet dry), this could be the one. Love this product? Check out our review of the best soccer cleats for our top picks.
Textile and synthetic lining for comfort and support
Waterproof material ensures dryness in wet weather
Wide foot opening to quickly put on and pull off
Removable insole to accommodate orthopedic demands
- BrandKenneth Cole
- ModelDesign 20015
- Weight14.1 ounces
Easily fits wider feet
Simple but stylish design goes with anything
Wide elastic panels for sufficient stretch
Quite lacking in arch support
If you’re not looking to break the bank, the best Chelsea boots in terms of value are the Hawkwell Formal Dress Casual Pull Up. The handmade material and soft TPU outsole ensure longevity and style, while the flexible design ensures consistent comfort for all day at the office.,
Its refined style is suitable for whatever look you’re going for, and unlike many boots we’ve selected, they have the bonus of running true to size. The material’s a littler thin, though, so they may not be great in winter, but such high-quality at an affordable-for-all price, do you really care?
Handmade material crafted with sophisticated technique
Soft TPU outsole ensures stability and longevity
High-cut ankle with elastic side panels and pull loop
Flexible design for consistent comfort
- Weight3.52 ounces
Stylish and refined for variety of looks
Run true to size for simple fit
Superb price for high-quality product
Thin material won’t keep your feet warm in winter
Only ever-so-slightly more expensive is the Metrocharm Cap Toe Formal Dress Casual which is a reliable shoe sure to last. The multiple panels, including a toe cap design keep them together, while the non-skid outsole provides stability on slippery ground.
However, they won’t fool more knowledgeable Chelsea boot enthusiasts and the material looks and feels a little too cheap compared to higher priced options. If you’re not too fussed about this, though, you’ll get a fine pair of shoes for the office or for your next date. Find more great products like this by checking out our guide to the best zero drop running shoes.
Extra panels over toe and heel provide durability
Cushioned footbed ensures comfort for all-day wear
Non-skid outsole keeps you stable
Sturdy synthetic materials keeps them looking like-new
- Weight12 ounces
Variety of colors available
Design suitable for formal, casual, and party occasions
Run true to size to ensure straightforward fit
Material looks a little too cheap compared to similarly priced options
The Cole Haan Bernard are a high-level and comfortable option for those who want to spend a little more on their footwear for guaranteed quality. At $150, they’re not cheap, but sometimes it’s okay to spend a little more to that extra peace of mind.
Our favorite feature is the small break-in period so you can show them off straight away, and unlike some boots, they arrive looking identical to the pictures. They’re also pretty waterproof, but don’t expect them to hold up great in harsher, colder, wetter conditions.
Fabric and leather lining keep feet warm in cold weather
Stretch side panels for easy put on and removal
Handy heel pull loop
Super comfortable for all-day wear
- BrandCole Haan
- Weight1.44 pounds
Little break-in period
Stylish design suits most occasions
Arrives looking exactly like the pictures
Water repellent but not great for harsher weather
A superb summer boot, the New Republic Chuck Suede provide an excellent lightweight option for casual occasions as you entertain friends and family at the yearly BBQ. The natural crepe outsole provides comfort and the leather lining and footbed ensures easy breathability.
The color doesn’t entirely match the pictures, so don’t start planning your summer outfit until they arrive, but the no-contrast elastic gives you a more neutral style that doesn’t seem too overbearing. If you like sports shoes check out our guide to the best basketball sneakers.
Elastic gusset with dual-color pull tab for easy wear
High-quality cowhide suede leather upper
Natural crepe outsole and padded insole ensures comfort
100% leather lining and footbed provides breathability
- BrandNew Republic
- Weight12 ounces
Neutral sand color ideal for spring and fall weather
Excellent option to match with worn jeans
No-contrast elastic ensures consistent style
Color not exactly how it looks in pictures
With a multi-panel design, the Bruno Marc Casual provide long-life on the upper whether you wear them daily or only pull them out the closet a couple of times a year. More of an outdoor shoe, the thick tread ensures stability but the flexible material still allows for superb mobility.
It’s available in a variety of colors and the slim fit design is suitable for both men and women. However, there are instances of the sole cracking, so take care where you step.
Multiple panel construction provide unrivaled durability
Thick tread outsole ensures stability on uneven ground
Easy wear heel pull tab
Flexible material ensures greater mobility
- BrandBruno Marc
- Weight12 ounces
Variety of colors offers something for every occasion and style
Excellent price considering quality construction
Slim fit design is suitable for men and women
Sole cracks at the heel
A top-quality boot, the Thursday Boot Company Duke is secure, stable, and reliable in both sole and construction for near-unrivaled performance and satisfaction. The cork footbed also provides comfort, while variety of colors mean you can find a pair for any season.
They may fit a little strangely for some, and when spending so much you want to be sure. If you trust the sizing before buying, though, you may be onto a winner. If you like working our check out our guide to the best crossfit shoes.
Studded rubber soles delivers greater grip on all surfaces
Premium construction for reliable durability
Flexible elastic goring makes them easy to put on and take off
Goodyear welt construction provides waterproofing and better stability
- BrandThursday Boot Company
- Weight12 ounces
Cork footbed forms to shape of feet for all-day wear
Multiple color options available for all seasons
Quite expensive but a worth-it investment for the long haul
May be slightly ill fitting for some
The SANTIMON Suede is a sleek shoe that’s definitely more at home for parties and similar functions if you want to stand out. It boasts moisture wicking material to keep your feet dry, while the long elastic gusset ensures it’s easily pulled on.
While slim, they stretch out after a few wears, but there’s still a little discomfort around the heel area. If you suffer from blisters quickly and without reason, it might be best to invest in some blister pads before wearing them.
Rugged rubber sole ensures easy all-day wear
Moisture wicking material keeps your feet dry
Breathable lining adds an extra layer of comfort
Easy grab pull on tab and long elastic gusset
- Weight12 ounces
Stretch out quickly despite feeling a little tight at first
Clean lines with near-perfect silhouette
Ideal height ankle height to fit easily with jeans
Heel area isn’t as comfortable as we’d like it to be
The Ted Baker Camroon 4 are our pick for the premium Chelsea boots for men and come with the flair and sophistication you expect. The rich paisley design on the gusset is a cool little detail that sets it apart, while the sleek leather upper further contributes to sophistication.
This allows for versatile functionality, even if they run a little small. You may enjoy the snug fit though to match your skinny pants, and if this is the case, then go for it. Don’t forget to also check our guide to the best cross training shoes.
Rich paisley design on elastic gusset adds extra class
Natural leather sole with branded emboss and authenticity
Large heel pull tab for easy wear
Sleek leather upper ensures sophisticated style
- BrandTed Baker
- Weight3 pounds
Versatile appearance for a variety of occasions
Reliable craftsmanship ensures quality performance
Snug fit around ankle prevents debris jumping into shoe
Run slightly small so go a size higher than usual
One of the easiest Chelsea boots to put on and take off, the Enzo Romeo BL01 Suede Leather is also one of the easiest to wear, too. The memory foam sock provides optimal comfort, while the flexible rubber outsole delivers great mobility.
Buy a size smaller than usual, though to make sure they fit, and when you do, you’ll get an excellent, stylish boot at a massively affordable price that might make you the talk of the town.
Twin elastic panel with increasing widths for easy pull on
Heel pull tab provides greater control
Memory foam sock for superior comfort
Flexible rubber outsole adds mobility and easy walking and standing
- BrandEnzo Romeo
- Weight2 pounds
Affordable price for excellent style
Upper portion stitched to inner sole for greater durability
Thin tread pattern is perfect for spring and fall conditions
Run half a size too large
Our final pick is the Ben Sherman Gaston which allows for easy foot entry with dual gore panels, and a soft printed fabric lining helps you foot feel at home inside. The classic Ben Sherman blue, white, and red accents make them easily identifiable, and show off your inner Mod like you’re fresh out of Quadrophenia.
Again, they run a little small, so a size up is advised, and doing this will give you a superb, lightweight boot that’s massively affordable for guys and girls who know exactly what they like. You may also like to check our guide to the best trail running shoes for men.
Easy slip entry with double elastic gore panels
Soft printed fabric lining provides comfort
TPR rubber outsole is both durable and flexible
Classic Ben Sherman color pull loop is easily identifiable
- BrandBen Sherman
- Weight12 ounces
Lightweight design prevent foot fatigue
Stylish for casual occasions and professional enough to wear at the office
Superb mid-range price for decent quality
Runs half a size too small for some wearers
Chelsea Boot Buying Guide & FAQ
How We Chose Our Selection of Chelsea Boots
Picking the best Chelsea boots isn’t as easy as it sounds. Luckily, we have these 3 criteria to help us make our final selection.
Reviews - Whether it’s the fit, the durability, the comfort, or how good they look, reviews are essential for helping us separate the good from the great.
Brand - Top brands offer top quality, but there are other smaller brands that often do just as good of a job while flying under the radar; we wanted to give them a shoutout so they know they’re appreciated just as much as the big boys.
Price - No one should miss out on great shoes just because they don’t fit their budget, so we found a wide range of options so everyone can look slick and sleek as we slide into summer and beyond.
Features To Look For In Chelsea Boots
Before making your final decision about which Chelsea boots are the best for you, why not consider these important features first?
Fit - An ill-fitting shoe can wreak havoc on your feet whether it’s too snug or too tight. Keep this in mind before buying so you and your soles don’t regret making this purchase.
Size - Some shoes run a little small, some a little big. You can usually tell from reviews and fitting advice, and you know your own feet, so select your size accordingly.
Material - Leather Chelsea boots are the classic, but if you’re not as down with leather as those of the past were, you can go for suede or synthetic, leather-looking materials. However, if this is the case, consider waterproofness, durability, and breathability.
Sole - Chelsea boots may have a grippy sole for different surfaces, or a flatter sole meant more for indoor wear around the office. You know what you’ll use them for, so don’t neglect to study the sole before buying.
Elastic Fastener - This needs to be stretchy enough that you can fit your foot in easily to put the shoe on and take it off, but also not too loose it feels like you’re wearing rain boots. Likewise, elastic that’s too tight can run against your skin and calf, causing discomfort.
Color - Not all colors go with all outfits, seasons, or occasions, so knowing when and where you’ll wear them will ensure you look the best you can.