- 1. Dr. Martens 2976 Chelsea Boots
- 2. Bruno Marc Philly Dress Chelsea Boots
- 3. Clarks Bushacre Hill Chealsea Boots
- 4. Steve Madden Highline Boots
- 5. Calvin Klein Larry Boots
- 6. Kenneth Cole Reaction Suede Boots
- 7. Hawkwell Formal Dress Casual Pull Up Boots
- 8. Metrocharm Cap Toe Formal Dress Casual Boot
- 9. Cole Haan Bernard Boot
- 10. New Republic Chuck Suede Boots
- 11. Bruno Marc Casual Boots
- 12. Thursday Boot Company Duke Boots
- 13. SANTIMON Suede Chelsea Boots
- 14. Ted Baker Camroon 4 Chelsea Boots
- 15. Enzo Romeo BL01 Suede Leather Boots
- 16. Ben Sherman Gaston Boot
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
Woven stretch goring inserts
Logoed pull-on loop at heel
Signature bouncing sole
Wide boot opening for easy wear
The iconic Dr. Martens 2976 is, 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 out our guide to the best shoe stretchers.
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
Ankle boot design offers support
Latex sole with solid tread
Fabric insole for consistent all-day comfort
Rounded toe suited to variety of occasions
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.
Suitable for both men and women
Flexible synthetic leather provides greater mobility
Plenty of room in the instep
Size runs a size too large
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
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.
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
Heel loop for easy wear and take off
Sophisticated stitching adds extra flair
Supple upper is flexible
Suede construction is long-lasting and durable
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.
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
Quality construction built to last
Easy to slip on and take off
Comfortable insole for all-day wear
Elegant design with multiple color options
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.
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
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
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.
Easily fits wider feet
Simple but stylish design goes with anything
Wide elastic panels for sufficient stretch
Quite lacking in arch support
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
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?
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
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
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.
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
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
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.
Little break-in period
Stylish design suits most occasions
Arrives looking exactly like the pictures
Water repellent but not great for harsher weather
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
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.
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
Multiple panel construction provide unrivaled durability
Thick tread outsole ensures stability on uneven ground
Easy wear heel pull tab
Flexible material ensures greater mobility
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.
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
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
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.
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
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
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.
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
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
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.
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
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
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.
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
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
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.
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
Chelsea boots made their famous debt in the 1950s and became exceptionally popular in the UK around the 1960s. English men were raiding stores and taking possession of their own pair of these stylishly comfortable shoes. It may be a classic, but it has stayed fashionable and relevant even up until these recent times.
Men who know style understand how much comfort, durability, and elegance a pair of Chelsea shoes would add to an already dapper ensemble. To ignore these fashion-forward boots is to seriously miss out on trendy, reliable, sturdy and stylish footwear that can be rocked both casually and formally.
Luckily, many of us do have the opportunity to mix up our style with these shoes; wearing them with a casual jean and top combo or rocking them with a suit and tie. These regal shoes add that shiny, polished look any gentleman would like to be associated with. Remember, these shoes are classics, and they have done a great job of making a fashion comeback in recent times.
So, if you’re going to add this to your collection, there are some key factors to be taken into consideration. We will be outlining some titbits, and shedding more light on these durable, sturdy fashion shoes called Chelsea boots.
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
With the resurgence of these boots in recent times, many brands have jumped on the bandwagon, manufacturing several shoes that match the image of what Chelsea shoes should look like. Due to this seemingly unimportant fact, individuals like us have to be well informed about what an actual Chelsea boot should have. To avoid unsatisfactory results or shoes that won’t last, we’ll be outlining some of the major features to look for in Chelsea shoes.
Material - Chelsea boots rock such a phenomenal design and are found to be made with different materials. Just like any pair of shoes, the materials used to make them are very important. They determine how long these stylish shoes will last, how easy it would be to maintain them as well as the comfort they re guaranteed to deliver.
One of the most popular materials used in making Chelsea boots is definitely leather. It’s the classic option, which features a smooth and sleek form. What’s more, they are easy to polish and keep shiny, with the advantage of matching practically any outfit. Leather tends to be easier to maintain and promises prolonged use.
The second material used to make Chelsea boots are suede material, which comes with a velvety texture to it. Suede Chelsea shoes are the go-to when looking for something more casual but still elegantly sophisticated. They go great with casual and smart outfits but may seem a bit to toned down for a more professional look. Suede may prove a bit more challenging to maintain, as they are not water-resistant or weather-resistant.
Design - A lot of people may have questions about adding this classic 1960s shoes to their modern-day look. With a simple look at the boots, there’s nothing outdated about them. However, understanding the design is the best way to know if Chelsea shoes are for you. First off, these shoes were crafted with one of the sole intentions being, easy wear-ability. Each pair should be easy to slide on without compromising the fit on the feet.
Chelsea boots achieve this with an upper that’s crafted with two pieces of leather; the vamp and quarters. the quarters which are the back of the shoe run all the way up to the ankles, with a tab that makes it easier to slide on the shoes. Below that is a small heel, and if you travel to the front, there’s the narrow, rounded toe-box. All these features are the signature of the perfect Chelsea boot. What’s more, the narrow toe box stylishly provides that sharp look, without being overly clownish or too pointy.
Size and Fit - Suede shoes are designed to slip right on without the hassle of laces or too much pulling and tugging. However, this free-form fit highly depends on getting the right size. There’s nothing more underwhelming than getting a small or bigger size of Chelsea shoes. These shoes are suited for the perfect fit; the wrong size will compromise your comfort, flexibility, and mobility. The narrow toe box suggests they may not be adequate room to maneuver if the size runs too small. Getting a larger size will compromise the support and flexibility these shoes are sworn to deliver. It’s best to check the size guides properly to ensure you’re getting the right size.
Chelsea Boot FAQ
Q: Are Chelsea boots comfortable?
A: Chelsea boots promise a very snug and comfortable fit, they shouldn’t be overly tight, but simply hug the feet adequately enough to keep a firm hold. The comfort they provide ride more on the individual; getting the right size is key. Smaller sizes may hurt the feet and make you think they are generally uncomfortable.
Q: What is the loop on the back of the boots for?
A: In addition to the elastic side panels, which are supposed to make Chelsea boot easier to slip on, there’s a tab on the back that enables the boots to be pulled on. Those pull-tabs make it more convenient to slip on the shoes without tugging at other corners to get them on.
Q: Can you wear chinos with Chelsea boots?
A: Chelsea boots go wonderfully with chinos; it all depends on how creatively you style them. Just like Chelsea boots, chinos are a pair of pants that can be worn for smart-casual events or formal outings. They are a little less formal than actual dressing pants but more elegant than a pair of jeans. Pairing them up with Chelsea boots will add a crisp, smart look that’s sophisticated without trying too much.
Q: Do you wear socks with Chelsea boots?
A: Yes, you can wear socks with Chelsea boots, especially if you want them to fit perfectly.