20 Best Men's Chelsea Boots To Wear In 2023 (2023)

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Published: Sunday January 8, 2023

Looking for the best men's Chelsea boots? You're in the right place.

20 Best Men's Chelsea Boots To Wear In 2023 (2)

Written by Hugo Whitehead

If you haven’t heard of the legendary men’s Chelsea boot then your wardrobe has been missing out on one of the most reliable and stylish footwear options for men today.

What makes the humble Chelsea boot so popular? Predominantly, its ability to seamlessly transition between both the casual and formal wardrobe. Men’s Chelsea boots can be worn with a suit just as well as a pair of jeans, with the only rule being that they should be well looked after to retain their polished appeal.

With an illustrious ancestry extending back to the British monarchy, the Chelsea boot design was conceived by J. Sparks-Hall, Queen Victoria’s personal shoemaker. Chelsea boots (which wasn’t named as such in the early days) proved popular with horse riders due to their durable nature and lack of laces to risk getting tangled.

A quick walk down memory lane shows that Chelsea boots for men were originally intended as riding boots, but the little band you may have heard of, The Beatles, would eventually wear them on stage – as well as The Rolling Stones – launching them into the menswear essentials lookbook until the end of time.

But what should you look out for when searching for the best men’s Chelsea boots?

In this Chelsea Boots story…

  • Men’s Chelsea Boot Materials
  • Chelsea Boot Styles
  • Chelsea Boot Last

Men’s Chelsea Boot Materials

The majority of Chelsea boots for men are going to be made from either leather or suede, with each material being better suited to winter and summer, respectively. Leather not only provides better protection against the winter elements of rain and snow, but it also moulds to your foot over time, making them more and more comfortable with each wear.

Suede, due to it being slightly harder to clean, is better suited to being worn in the summer months where they’re going to be less at risk of stains and rain. You’re more likely to find suede Chelsea boots in a wider range of colours too, so plenty of space for showing off your true colours.

Chelsea Boot Styles

As with any boot, men’s Chelsea boots can be styled in various ways. You can find Chelsea boots that end at the ankle, or finish above it. The higher the fit the easier the Chelsea boots are to wear with a suit as the top can be covered by your pants. Lower-fitting styles will end up showing more skin when you sit down, and nobody really wants that.

The style of the toe can differ from pair to pair too. Rounded toes are the perfect all-rounder, meaning they can be worn up or down, depending on the situation you find yourself in. Pointed toes are a harder style to pull off, and you’ll likely see these on the feet of mod-rockers and the more ‘rebellious’ types. Of course, they also lend well to more formal occasions.

Chelsea Boot Last

When searching for a pair of men’s Chelsea boots, you’re likely going to come across the term ‘last’, particularly with pairs from the more high-end manufacturers. A last is a solid form around which the boot is moulded. You’ll see a number associated with a particular last, and this could be exclusive to a particular brand, your knowledge of a brand will come good here. Although, if you’re not entirely sure what each last means for each manufacturer, a visit to a store or a quick email will help you out.

With the resurgence of the Chelsea boot in the men’s fashion space, there’s no shortage of materials, colours and price points to choose from. Thankfully we’re about to make your job easier with a selection of the best Chelsea boots for men to buy right now. And once you’ve done that you can learn how to wear and style them.

  • Boots For Men
  • Men’s Winter Bootst
  • Suede Boots For Men

Our selection of Chelsea boots…

Oliver Cabell

20 Best Men's Chelsea Boots To Wear In 2023 (3)1/24

Price: From $292
Sizes: 7-13
Material: Italian suede
Customer Reviews: “These boots are amazing value for the price. Light weight and durable, it’s like walking on clouds.”

Oliver Cabell is a footwear brand all men worth their stylish salt should be aware of. Not only, like Common Projects, does Oliver Cabell produce a suitably sexy range of sneakers, but it too has some serious men’s chelsea boots to boot. Take this pair, finished in a rather unique truffle colour. The leather and suede that has gone into their construction has been sourced from Italy, before being hand stitched in Spain. Unusually for a luxury brand, Oliver Cabell breaks down the cost of making each pair of boots, so you can see exactly where your money is going. A well-made pair of boots and ethical production? Sign us up.


20 Best Men's Chelsea Boots To Wear In 2023 (4)2/24

Price: From $315
Sizes: 39-48
Material: Leather
Customer Reviews: “The calf leather on these handmade boots are soft and high quality, and the boots are very comfortable to wear. I was very happy with Scarosso.”

Scarosso makes all of its shoes in Montegranaro, Italy and promises to offer customers Italian design and craftsmanship, but without the high price tag commonly associated with such factors. Generally, because of their low margin approach to sales, shoes and boots can only be found in the most popular colours (think blacks and browns) and the same goes for the selection of men’s Chelsea boots.

The Hunter Chelsea boots are modelled on a classic British design and benefit from the Blake Rapid welt for the sole (which introduces a midsole compared to a standard Blake welt, making the Chelsea boots more water resistant). You also get a generously large elasticated side and small nubs on the soles for added traction.

(Video) THE 10 BEST CHELSEA BOOTS FOR MEN | Casual, Formal, Work, Cheapest, Rarest, and More

Cole Haan

20 Best Men's Chelsea Boots To Wear In 2023 (5)3/24

Price: From $228
Sizes: 7-16
Material: Leather
Customer Reviews: “Very comfortable, stylish and a color I can wear with many outfits. Job well done Cole Haan.”

From casual, comfortable walking shoes to waterproof sneakers and everything beyond, Cole Haan is a trusted producer of quality footwear. The American brand isn’t afraid to experiment with design, either, as proved by its immensely chunky soles found on select sneakers and boots.

This pair of Gramercy men’s Chelsea boots are far more conventional in their approach, however, being made from premium calf leather, more leather for the lining and a leather sole with added rubber so you don’t go sliding when out on the streets. The company’s own Grandføam can be found in the footbed to provide an extra layer of cushioning, meaning you can wear this leather men’s Chelsea boot all day long.


20 Best Men's Chelsea Boots To Wear In 2023 (6)4/24

Price: From $195
Sizes: 7-13
Material: Leather
Customer Reviews: “Very good looking shoes that are as comfortable as tennis shoes and as supportive as high quality walking shoes. Haven’t had them long but if these hold up this brand will be my go to.”

If you haven’t already heard of Amberjack, then you really should sit up and pay attention. Based in Brooklyn, New York, Amberjack designs some of the most comfortable men’s footwear out there. Using proprietary designs and materials, the company’s Chelsea boots are quite unlike any other you would’ve slipped your feet into.

Aptly named, The Chelsea is a boot that benefits from a sole that combines flexibility and support, to ensure your feet remain comfortable all day long. Heat-activated arch supports provide a memory foam-like feel when you’re walking, and a super soft sheepskin lining only adds to the extreme level of comfort. But, perhaps best of all, is just how little The Chelsea costs, considering what you get. For just under $200, you can own what could be the most comfortable pair of Chelsea boots for men on the market.


20 Best Men's Chelsea Boots To Wear In 2023 (7)5/24

Price: From $120
Sizes: 7-13
Material: Leather
Customer Reviews: “Very happy, great quality, comfortable and looks great. Women like them too.”

Clarks is an absolute boss when it comes to footwear. The British-based brand may be known, in the UK at least, for providing school kids with their back to school essentials, but it should never be overlooked as a provider of quality footwear. With suede and leather options, you can easily score yourself a men’s Chelsea boots for both summer and winter. The Gobi is an ideal summer staple, being made from a sumptuous suede nubuck leather for the upper, with a full grain leather liner to cuddle your foot in ultimate comfort. Clarks’ leather and rubber hybrid sole provides just the right amount of bounce and comfort, while also providing great traction.


20 Best Men's Chelsea Boots To Wear In 2023 (8)6/24

Price: From $219
Sizes: 8-13
Material: Cow suede
Customer Reviews: “They have great styles and fits.”

British fashion label AllSaints sure does know how to make stylish clothing and footwear. A brand popular with famous faces around the world, AllSaints is known for its rebellious and biker-style, as well as its use of high-quality materials. The Harley Chelsea boots use a mixture of 100 per cent cow suede and goat leather in their make up, and are finished in either black or charcoal gray. In typical AllSaints fashion, these colour finishes are ever so slightly edgy, making them perfect to wear with skinny jeans and a leather biker jacket.

Dr. Martens

20 Best Men's Chelsea Boots To Wear In 2023 (9)7/24

Price: From $160
Sizes: 6-12
Material: Leather
Customer Reviews: “Martens and I am in love! They are a little stiff at first, but once they break in they are so comfy and stylish!”

Some of the most recognisable boots in the business hail from Dr. Martens. The British brand’s iconic sole with yellow stitching is particular favourite of punks and goths, although they’ve also found an affinity with those who simply value comfortable boots that can be worn for hours and hours.

While the lace-up version is undoubtedly the most common you’ll see, it hasn’t stopped ol’ Doc from taking them away to create a Chelsea boot. Benefitting from the same Air Cushion sole that makes them so popular, these men’s Chelsea boots are unmistakably DMs from a distance and rock full grain leather while remaining entirely affordable.


20 Best Men's Chelsea Boots To Wear In 2023 (10)8/24

Price: From $125
Sizes: 7-13
Material: 100% Nylon
Customer Reviews: “Very comfortable and very durable. They keep my feet both dry and warm.”

British brand Hunter is known worldwide for its Wellington boots (galoshes or gum boots for international readers) although during its infancy as a company in the 1850s, the company can be considered inventor of the car tyre we know today. The company is now an expert in the use of rubber for footwear, which has allowed it to create more than just humble Wellingtons.
Such as this slim fit Chelsea boot. Constructed from the same rubber that has made Hunter famous, these men’s Chelsea boots adopt a more classic Chelsea boot style, including heel tab. The use of rubber makes them completely waterproof too, making them potentially the perfect pair for city workers in winter.


Rhodes Footwear

20 Best Men's Chelsea Boots To Wear In 2023 (11)9/24

Price: From $198
Sizes: 8-13
Material: Leather
Customer Reviews: “They’re one of our favorite styles of men’s boots because they’re as comfortable as walking on a cloud, and they look damn good.”

American bootmaker Rhodes says its boots are designed for those who love to wear a high-top day in, day out, no matter what they’re doing. The company adds they may not compete with whatever fancy and flashy pairs you may also own, but then you would only wear those to high-end occasions. Rhodes handcrafts each pair of boots in either Portugal, Italy or Mexico using calf leather and suede, to result in boots that age gracefully over time.

The Huxley adopts a classic look (and even gets dual pull-tabs) and, being polished as they are, can allow you to wear them with either a suit for formal events or a simple pair of jeans and a t-shirt for weekends on the ranch. A Texon insole with insulation and anti-shock foam gifts all-day comfort, and they’ll even fit like a glove straight out the box. Although, given a week or two of wearing in you’ll forget you have these Chelsea boots on.

ASOS Design

20 Best Men's Chelsea Boots To Wear In 2023 (12)10/24

Price: From $58
Sizes: 5-14
Material: Leather
Customer Reviews: “No regrets! A versatile pair of boots. Wear it for an evening with the guys or with the wife.”

British clothing retail giant ASOS is a one-stop shopping destination for practically everything you can think of. With virtually all major brands stocked, including some high-end designer, ASOS makes it easy to do all your shopping online.

The company’s own ASOS Design label stocks many of the classic styles and charges a fraction of the price of more prestigious and recognised brands. These brown leather men’s Chelsea boots with contrasting sole look just as good, however, making use of real leather for the upper. Sure, they might not provide as many years of service as some others, but when you’re paying a quarter of the price (or less in some cases) you can’t really complain.


20 Best Men's Chelsea Boots To Wear In 2023 (13)11/24

Price: From $305
Sizes: 6-14
Material: Leather
Customer Reviews: “They are pretty sturdy construction. They seem pretty rugged. I will say that the quality control isn’t the best.”

Mexican bootmaker Unmarked takes its time producing each individual pair of boots, but for good reason. For starters, they’re all handmade at the factory in Leon, Mexico, but on top of that, the vegetable-tanned leather used is put through a slow process from being cut to eventually being moulded into the boots that arrive at your door. They’re a product of love that you can truly feel whenever you put a pair on.

They’re great-looking too, such as the Toro, which use bull hide leather and a storm welt construction. This is an extension of the Goodyear, as it is wider to allow for a more solidified seal to help prevent water from leaking in. Available in a range of colours, these Chelsea boots are ideally suited to being dressed down with jeans or worn underneath a suit.

Hugo Boss

20 Best Men's Chelsea Boots To Wear In 2023 (14)12/24

Price: From $250
Sizes: 7-13
Material: Cow leather
Customer Reviews: “These boots feel great to the touch, the leather is supple and moves great on the foot.”

You can always rely on German fashion label Hugo Boss to inject a little quirkiness into their pieces, providing customers with a chance to stand out from the crowd with unequivocal German style.

This pair of Chelsea boots from Hugo are a prime example. Rocking a conventional suede silhouette, they also receive a neoprene treatment to provide some elasticity so that you can slide them onto your feet.


20 Best Men's Chelsea Boots To Wear In 2023 (15)13/24

Price: From $155
Sizes: 7-15
Material: Leather
Customer Reviews: “Love every pair of Keen except for one. Not bad considering I have over 20 pairs.”

Founded in California in 2003 but now calling Portland, Oregon home, Keen is a footwear brand that is particularly well suited to the outdoors, thanks in part to the rubber toe bumper found on the majority of its shoes and boots (as well as the Newport Sandal first launched in 1999).

(Video) How To Style Chelsea Boots As An Adult Man

Just on first impressions, the 59 II Chelsea boots look like a tough, rugged outdoor boot and that’s exactly what they are. Premium full-grain nubuck leather protects your feet from dirt and water, while a cushioned midsole makes them comfortable enough for extended walks and hikes. Basically, they’re a pair of men’s Chelsea boots that are more than happy to be treated roughly and thrown around a bit. So have at it.


20 Best Men's Chelsea Boots To Wear In 2023 (16)14/24

Price: From $215
Sizes: 7-14
Material: Nubuck leather
Customer Reviews: “This brand never disappoints. Don’t hesitate to buy this boot.”

Italian brand Astorflex has been producing footwear since the 1800s and has often been credited with making “the best desert boots in the world.” Now in its sixth-generation of family ownership, the company strives to be as ecologically-friendly as possible. The Bitflex is a standout model in the company’s lineup. Taking the traditional Chelsea boot silhouette, Astorflex has given it a memory foam footbed for super soft strides and a ventilated elasticated side panel for sliding them on and off with ease, and for improved breathability. With virtually every colour option you could want being available, you may want to start stocking up.

Common Projects

20 Best Men's Chelsea Boots To Wear In 2023 (17)15/24

Price: From $625
Sizes: 39-47
Material: Leather
Customer Reviews: “Personally, I absolutely love them. They are more for casual wear, but they are super comfortable and great for most terrains.”

Not just one to rest on its minimalist white sneaker laurels, Common Projects, being a footwear brand first and foremost has a solid offering of Chelsea boots. This suede pair for example has all the makings of a pair that screams premium. Not only are they on the perfect side of minimalist – a skill Common Projects is a master of – but they use high-quality materials and colours to make them one of the most versatile pairs of Chelsea boots you’ll ever come across. In true CP fashion, the style, colour and size is stamped on the heel.


20 Best Men's Chelsea Boots To Wear In 2023 (18)16/24

Price: From $385
Sizes: 6-11
Material: Calf leather
Customer Reviews: “The suede is nice and even and soft, and the stitching is very nicely done. I like that it’s white contrast stitching.”

British footwear brand Grenson has been fitting the feet of the world for over more than 150 years. It’s no wonder then that it has taken the Chelsea boot and given it its own special twist. The Declan for example is an exquisitely made pair of leather Chelsea boots, using calf skin leather for their upper and a single piece of leather for their sole. Exhibiting a slightly pointer toe than some other pairs on this list, the Grenson Declan are perfect for those who continue to champion the mod-scene style.

Zonkey Boot

20 Best Men's Chelsea Boots To Wear In 2023 (19)17/24

Price: From $1,015
Sizes: 5-12
Material: Calf leather
Customer Reviews: “Nice! I have a few pairs of Zonkey Boots and I love them. Hand-welted, skinny waist, high quality leather and a relatively reasonable price.”

Austrian footwear Zonkey Boot was founded in 2011 with good reason for choosing such an elaborate name. Referencing the donkey/zebra crossbreed, Zonkey Boot aims to combine traditional handcrafting techniques with designs that verge more towards casual and fashionable, as opposed to traditional.

The ZeroThreeThree boots, however, look entirely traditional in their design, but they are oh so lovely. Made from Bavarian Calf leather and hand stained, these Chelsea boots will caress your feet in absolute comfort. A calf leather lining and bovine leather insoles add to their luxuriousness, while also being breathable.

Paul Smith

20 Best Men's Chelsea Boots To Wear In 2023 (20)18/24

Price: From $830
Sizes: 6-11
Material: Calf leather
Customer Reviews: “These boots are gorgeous. Understated and sleek. A hint of gleam in the elastic which is barely noticeable.”

Continuing the domination of the British labels is Paul Smith. The fashion designer is regularly associated with the impeccably dressed gentleman, providing everything from well-fitting sweaters to must-have bags. The same goes for its Chelsea boots, with all manner of styles and materials being used to cater for the style-minded man. We love these brown suede Canon boots for their just-above-ankle fit and rounded toe. Colour-matching elasticated side panels and soles add their premium look, while the flush-sitting heel tab gives them an overall more streamlined look.

To Boot New York

20 Best Men's Chelsea Boots To Wear In 2023 (21)19/24

Shop at toboot.com - From $425

(Video) Best Men’s Chelsea Boots you van by on

Price: From $425
Sizes: 7-13
Material: Calf leather

To Boot New York is a footwear brand that hails from America. With footwear-specialist Adam Derrick at the helm, each season’s drop encapsulates what consumers look for is a new pair of shoes, sneakers or boots. Leathers are sourced from France or Italy, where they’re hand-selected and hand-cut to ensure you, the customer, receives only the very best. If you’re after a pair of luxurious brown leather Chelsea boots, To Boot has you covered with the Shelby. With a low-cut fit that makes them easy-as-pie to take on and off, they’ll happily accessorise any casual or formal outfit. They benefit from a Blake stitch, which sees the outer sole stitched directly to the inner, making them more lightweight than Chelsea boots that use the Goodyear welt.


20 Best Men's Chelsea Boots To Wear In 2023 (22)20/24

Price: From $619
Sizes: 6-11
Material: Leather
Customer Reviews: “Very good and legendary shoes.”

Tricker’s is Britain’s oldest shoemaker, having been in business for more than 190 years. Every single pair of Tricker’s is made from start to finish at the company’s factory in Northampton, England; a practice which it has carried out ever since its founding. That therefore means you receive a quality product, such as the Lambourn. Made to resemble a Jodphur boot – a Chelsea boot made to be a riding boot with a rounded toe and heel – they’re equal parts casual and formal. An extra tab on the front of the foot opening helps you slide them on, and once you do, you won’t want to remove your foot from the 100% leather lining.


20 Best Men's Chelsea Boots To Wear In 2023 (23)21/24

Price: From $1,290
Sizes: 5-13
Material: Calf leather
Customer Reviews: “Feels very plush ⋅ Extremely well-made.”

For yet another luxury option for all your Chelsea boot needs, avert your gaze on to Church’s. This British brand has been in business since 1873, remaining one of the dominant shoemaking forces in the Northampton area. Today the company produces around 5,000 pairs of shoes each week, the majority of which are shipped to international countries. They may be a tad more expensive than some other pairs of Chelsea boots on this list, but you’re paying for outright quality, such as this pair of Dixton boots. They employ a Superbuck upper and the company’s Last 173 fit. Church’s branding can be found inside and on the sole to let everyone else know how entitled you are.

R.M. Williams

20 Best Men's Chelsea Boots To Wear In 2023 (24)22/24

Price: From $539
Sizes: 2-13
Material: Italian leather
Customer Reviews: “The leather is exceptional quality and the comfort is superb for a pair of boots. Plus, the materials used balance style with rugged durability.”

Synonymous with Australian Outback culture, R.M. Williams is one of the master producers of leather boots. With an esteemed history and age-old production techniques still being used today, when you buy a pair of RMs, you’re investing in something of top-quality, that has been handmade from start to finish. The Craftsman boot is the iconic RM version of men’s Chelsea boots that adorns the feet of Australians everywhere, as well as international consumers who know quality when they see it. They’re from a supple Yearling leather, and in true RM style, are made from a single piece, stitched together at the back. A Goodyear welt is used to provide the ultimate in waterproofness and durability, although it also allows them to be resoled should you ever need to.

Crockett & Jones

20 Best Men's Chelsea Boots To Wear In 2023 (25)23/24

Price: From $750
Sizes: 7-14
Material: Calf leather
Customer Reviews: “Great all around boot – goes with suits to jeans. Highly recommended.”

If you still don’t think there’s a British boot maker for you, maybe Crockett & Jones will be able to charm you. Another centuries-old company, being founded in 1879, the footwear company is a champion of the Goodyear welt, ensuring all its shoes are weatherproof and durable. C&J must be doing something right, as Daniel Craig’s James Bond wore its shoes in Skyfall. For a classically-styled pair of Chelsea boots, Crockett & Jones has just the thing, with the Goodyear welt remaining a defining feature, this pair of black wax calf leather Chelsea boots will happily protect your feet during winter. A rubber sole ensures you remain planted to the ground and their streamlined look allows them to be dressed up or down.


20 Best Men's Chelsea Boots To Wear In 2023 (26)24/24

Price: From $180
Sizes: 4-15
Material: Leather
Customer Reviews: “These are very comfortable and fit my need for a wider toe box well. Really happy with them so far.”

All of Veldskoen’s shoes are handcrafted in South Africa with locally sourced, premium materials. The brand is committed to crafting shoes that are not only ethically and responsibly made but, feel crazy comfy and provide effortless daily style.

Veldskoen has a small but mighty range of Chelsea boots that are extremely stylish and well-made.


(Video) 20 Chelsea Boots Outfits 2023| Men’s Fall & Winter Outfit Inspiration 2023


Are Chelsea boots still in style 2023 for men? ›

Sleek and sophisticated, Chelsea boots lend themselves to many outfits, whether you're adding a rock 'n' roll flavour to tailoring or a rugged edge to weekend attire.

Are Chelsea boots in style 2023? ›

Women's Chelsea boots are always in style, making them a timeless addition to any wardrobe. As we dive into the latest fashion trends of 2023, Chelsea boots are emerging as a popular choice in footwear.

How to wear Chelsea boots in 2023? ›

Chelsea Boots and Dresses

These boots will also look good with midi dresses, leather or denim. Just make sure that your boots are high-raised. As for slip dresses, pair them with chunky boots. You can also add a moto jacket or a long and soft sweater to give the outfit an edgy vibe.

What boots will be in fashion 2023? ›

Faux snake finishes and prints on boots never feel too tethered to a particular season, but make no mistake, they're going to be big news in 2023. Style Notes: Traditional grey colourways will go with a multitude of outfits, while the warmer python prints at Rejina Pyo and Bally present a fresh take on the trend.

What to wear with boots in 2023? ›

Wide-leg pants and loose denim may be some of the trendiest pant options right now, but one item they don't play nicely with is winter boots. Leggings, skinny jeans or other slim-fit pants will fit much more smoothly into the shaft of your boot and create a nice lean line that elongates your legs.

How to wear jeans with boots in 2023? ›

TLDR: You can wear ankle boots with skinny jeans that are tucked in, rolled under or with a pair of jeans that hits at the ankle. The same rule applies for straight-leg jeans. If your booties are short, don't tuck them in. If your booties are tall, they'll look best with tucked-in skinny jeans.

What pants go with Chelsea boots? ›

With Chelsea boots, wide-leg pants, cropped pants, palazzo pants, leather pants, slim dress pants and cargos all look great. The key is to find the right balance between proportion and silhouette. For a streamlined look, pair black Chelsea boots with black slim dress pants.

What to wear with chunky boots 2023? ›

Pair them with skinny jeans or a wide leg pant and a long sweater, topped with a long coat or a puffer jacket. This look is perfect for casual outings, running errands, or even a cozy night in. Mini Dress: For a more feminine look, pair your chunky boots with a mini dress.

What is the best color for Chelsea boots? ›

Brown in all shades is ideal for a pair of Chelsea boots, since it can be easily dressed up or down. If you want to go formal, pair your Chelsea boots with suits in mid to and light tones for the best results.

What Colour Chelsea boot is most versatile? ›

Black Chelsea boots (above) have always been very popular and the classic choice. They go with many so many outfits. You can wear them for work and they look as good after hours and at the weekend. They can be worn with a suit, jacket, chinos or jeans, and this probably makes them the most very versatile.

How to wear Chelsea boots for men? ›

You can choose Chelsea boots of any material & pair it with any casual chinos or a pair of jeans. You can also wear it with a casual shirt, a T-shirt & throw on a jacket for the perfect men's Chelsea boots outfit.

What jeans should men wear with Chelsea boots? ›

If you are planning to go for formal occasions, you should prefer dark-wash jeans with Chelsea boots having a dark color. Dark-wash jeans enhance a great look with dark Chelsea boots. If you are planning to style your Chelsea boots for casual occasions, you should prefer wearing light-wash jeans.

Should men tuck jeans into Chelsea boots? ›

The main thing to note is that for a sleek look, we wouldn't recommend tucking your trousers into your Chelsea boots. Instead, for a classic silhouette the hem (cuffed or not), should sit neatly just over the tops of your boots. Jeans, chinos, straight-leg trousers, they all work!

Should I buy Chelsea boots a size bigger? ›

Buy your correct size and no bigger.

Chelsea boots are normally true to size, so there's no need to size up or down.

Do men still wear Chelsea boots? ›

Chelsea boots are a wonderfully simple and versatile style of men's boots. Depending on what they're made from and how they're constructed, they have the possibility to be either very elegant or ruggedly casual boots, making them a great addition to your wardrobe.

Should guys wear Chelsea boots? ›

These boots are highly versatile & can be paired not only with casuals but can also be worn as a business casual. The key to any men's guide to wearing Chelsea boots as a business casual is balance. You can choose any leather pair of boots, & pair it with chinos, a blazer & a casual shirt.

Are Chelsea boots back in style? ›

They remained a popular style until the beginning of the 20th century. After gaining traction again in the 1950s, they were worn by stars such as The Beatles and The Rolling Stones. In the past few years, Chelsea boots have made a comeback and are a highly admired shoe trend this winter.


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