The Chelsea boot is an unlikely marriage of rock ‘n’ roll swagger and practicality. Aussie farmers love them, but it’s been bridging that gap for generations. These elasticated leather workhorses are not only pretty but also super versatile and deserve a place in the Footwear Hall of Fame.
The Chelsea boot is an all-rounder. It is a partner to your tailored suits and a weekend wardrobe staple. Every stylish gent should have one in his shoe collection. In this guide, we’ll look into the history of the Chelsea boot and where to find the perfect one for you.
What are Chelsea Boots?
You may already know of other boot styles, but if you don’t, let us break it down for you. A Chelsea boot is an ankle-high leather boot with elastic panels on either side. These panels allow you to slip the boots on and off with ease, style, and convenience.
The Chelsea boot was originally made by Queen Victoria’s shoemaker, J. Sparks-Hall, who said, “She (Queen Victoria) wears them daily and thus gives the strongest proof of the value she sets on the invention.” Initially, the boots were for horse riding and walking, and thus, more robust versions with thick rubber soles and even steel toe caps were developed for workwear.
Forward to the 1950s and 1960s, Chelsea boots became a fashion icon, largely thanks to the Swinging London scene. Their association with the city, particularly the King’s Road in Chelsea and Fulham, is believed to be the origin of the name. Today, Chelsea boots are a stylish choice; heritage meets modern fashion.
How to Style Chelsea Boots?
One of the best features of Chelsea boots, apart from their clean and minimalist design, is their versatility. These boots are the perfect footwear for a man who wants to go from work to play and everything in between.
Office
Whether your workplace requires a full suit or a T-shirt and jeans, a pair of Chelsea boots will dress up your look. These boots add a bit of flair and sophistication and are versatile for any office environment.
Corporate
For corporate offices, go for a sleek leather Chelsea boot. When choosing the color, match it with your suit. For example, a navy suit with brown Chelsea boots or a grey suit with black Chelsea boots. I love how this attention to detail not only dresses up the outfit but also shows a sense of style. The right footwear can boost your confidence in a professional setting.
Trousers
Make sure your trousers break at the right place. The hem should sit just above the ankle so there’s a clean line and no boot top showing. This creates a streamlined look that matches the Chelsea boot’s design. I find this small detail makes a big difference in how put together an outfit looks.
Business Casual
For a more relaxed business casual look, team brown suede Chelsea boots with black denim and a flannel shirt. This combination is the perfect balance of comfort and style and is good for casual Fridays or less formal meetings. The suede adds texture and warmth, and the flannel shirt keeps the outfit approachable yet polished. I wear this combination when I want to be comfortable but look sharp. It’s a way to express some personality while still being professional.
Party
For social events like cocktail parties, weddings, or a big date, Chelsea boots are an elegant footwear option that will dress up your look. Their clean design makes them a versatile choice that will go with many outfits, so you’ll always be stylish for any occasion.
Stylish Outfit Ideas
For an outfit that works for all these occasions, go for an eye-catching suit or contrasting trousers and blazer separates. A well-fitted suit in a bold color or unique pattern will make a statement while contrasting trousers and a blazer will give a more relaxed yet sophisticated look. I love the look of a deep navy blazer with lighter trousers. It’s a classic combination that always feels modern.
Add a Tonal Roll-Neck
To add an extra layer of polish, try a tonal roll-neck underneath your blazer. This will add warmth and a bit of sophistication to your outfit. A roll-neck in a matching color will create a clean line that draws the eye to your overall outfit. I wear charcoal or cream roll-necks as these colors go with many blazers and suits, so they’re super versatile.
The Chelsea Boots
Complete your look with a leather Chelsea boot. Go for a polished black or rich brown, depending on your outfit’s color. The clean lines of the Chelsea boot will match the tailored elements of your outfit, so you’ll look sharp from head to toe. I find investing in a good pair of Chelsea boots not only dresses up my outfit but also provides comfort for the whole evening, which is important for long events.
Casual
The Chelsea boot is a casual shoe, so it’s a great everyday option. Its versatility will go with many outfits, from selvage jeans to chinos, and can be dressed up or down depending on the day’s activities.
Effortless Everyday
For a no-fuss look that requires minimal effort, go dark-wash jeans with a white T-shirt. This classic combination is stylish and comfortable. To add an extra layer of polish, throw on a suede jacket or an overshirt. I love how this outfit is casual yet polished enough for running errands or meeting friends for coffee.
Smarter Casual
If you want to look a bit smarter, try cotton twill khakis with an Oxford button-down shirt and a lightweight sweater. This will dress up your look without being too formal. To finish the outfit, add a blazer or a leather motorcycle jacket for an extra bit of style. I find a well-fitted blazer can turn a casual outfit into something that feels more put together, perfect for casual Fridays at work or dinner out.
The Best Brands For Chelsea Boots
Now that you know Chelsea boots and how to wear them, it’s time to explore the best brands that offer good investment options. Each of these brands offers something.
Velasca
Key Style: Magut
If you want an Italian-made Chelsea boot that’s the epitome of sprezzatura, look no further than the artisanal brand Velasca. Their Magut boot is made from full-grain, smooth calfskin leather, so it feels luxurious and looks sophisticated.
What makes the Magut stand out is the sturdy Vibram rubber sole, which is not only grippy but also durable. This combination of elegance and durability makes the Magut perfect for winter wear, so you can brave the elements without sacrificing style.
I like that Velasca focuses on craftsmanship and quality, so its boots are worth investing in for anyone looking to upgrade their shoe game. Whether you’re dressing up or keeping it casual, the Magut boot is versatile and timeless and will go with many outfits.
Oliver Cabell
Key Style: Chelsea Boot
After building a reputation for making luxe, minimalist sneakers without brand markups, Oliver Cabell has branched out into more formal footwear. However, it still keeps its pricing transparent.
Their Chelsea boots take the classic shape and elevate it with high-quality Italian leather, making them durable and stylish. I like Oliver Cabell’s Chelsea boots because they’re sleek and sophisticated, making them suitable for many occasions.
Despite looking refined, these boots are highly wearable every day so that you can wear them in your daily wardrobe. Whether you’re going to the office or out for dinner, Oliver Cabell’s Chelsea boots are the perfect blend of elegance and comfort, so they’re a great addition to any stylish gent’s wardrobe.
Myrqvist
Key Style: Chelsea Boot
Goodyear welted construction at an affordable price is hard to find, but Myrqvist, based in Stockholm, makes it possible. Their Chelsea boots are hand-made in Portugal, so they are high quality and have excellent craftsmanship.
Myrqvist offers many styles to suit different tastes and needs. Some are made from one piece of leather for a sleek and seamless look, while others are winter-ready with a commando sole for extra grip and durability in harsh conditions.
I like that Myrqvist combines traditional with modern, so their Chelsea boots are stylish and practical for everyday wear. Whether you want a classic or something more rugged for winter months, Myrqvist’s Chelsea boots deliver both quality and design, so they’re a good investment for any shoe collection.
Kleman
Key Style: Tonnant
The French brand Kleman brings a rugged and tough look to the Chelsea boot market, different from the traditional ones. Their Tonnant style has chunky silhouettes, often on a commando sole, so they look like work boots but are durable and stylish.
Not all of Kleman’s styles are so tough; some have dramatic collars and come in unique materials like faux snakeskin burgundy leather. This gives you many options, from bold and edgy to refined and sophisticated.
If you’re looking for a Chelsea boot that’s different and will add some flair to your shoe game, Kleman is a great place to start. Their innovative designs and quality make them a great choice if you want to make a statement with your boots.
Common Projects
Key Style: Suede Chelsea
Common Projects, the Italian-American luxury footwear brand famous for its premium sneakers, has extended its expertise beyond athletic footwear. While it is best known for its iconic Achilles Low shoe, its Chelsea boot has also become a classic in the high-end footwear world.
When you buy a Common Projects Chelsea boot, you can expect only the best materials and Italian craftsmanship. The gold numbering on the heel is their signature and adds a touch of elegance and authenticity, making these boots instantly recognizable.
The suede version is an easy-to-wear everyday option that combines comfort with style. I like the softness of suede, which adds a relaxed yet sophisticated look, so these boots can be worn with casual or more dressed-up outfits.
Amberjack
Key Style: Chelsea
Designed in Brooklyn, NY, and made in one of Portugal’s top factories, The Chelsea by American brand Amberjack is probably the most technical boot on this list. Made from the best leather from the world’s top tanneries, of which Amberjack is a partner, these boots are proof of mastery.
What really sets Amberjack’s Chelsea apart is its technical features. The boots have heat-activated arch support, so you’re comfortable all day, whether you’re on your feet at work or out for a night. The laser-perforated uppers are breathable for various climates.
The proprietary outsole is mechanically designed to support where you need it most, so it’s long-lasting and durable. I like that Amberjack combines style with functionality, so The Chelsea is not only a fashion choice but also a practical one for everyday wear.
Saint Laurent
Key Style: Wyatt
You can’t mention Saint Laurent without talking about their iconic boots, and you can’t have boots without the influence of this French fashion house. The Wyatt has been a staple in Saint Laurent’s collections for years. It is a sleek and simple design that oozes Parisian chic.
The Wyatt boots are best worn with slim black denim and a classic black leather jacket for a timeless look that’s effortless sophistication. I like how this combination shows off the boots and creates a cohesive outfit that’s edgy and refined.
If you want to take it to the next level, wear all Saint Laurent, and you’ll get an extra layer of authenticity. The craftsmanship and attention to detail in Saint Laurent’s designs mean the Wyatt boots are not just a fashion statement but a wardrobe staple. If you want to be that Parisian, then Wyatt boots are a must-have!
Tricker’s
Key Style: Henry Brogue
Based in Northamptonshire, Tricker’s is a shoemaker with a long history and serious credentials. Since 1829, the brand has been the go-to manufacturer for heavy-duty country footwear for England’s estate owners and landed gentry.
But the Henry Brogue is not your average low-profile, slim-fit Chelsea boot. It has commando soles and brogue detailing for a unique look. Premium craftsmanship is visible in the Goodyear-welted soles and hand-stitched uppers, which ensure durability and longevity.
I like that Tricker combines traditional methods with functional design, so their boots are not only stylish but practical for various terrains. If you want a Chelsea boot with character and quality, the Henry Brogue from Tricker’s is a great choice that’s both heritage and modern.
Grenson
Key Style: Declan
Goodyear welting is a historical process, and Grenson was the first brand to use it. Based in Northamptonshire, Grenson is one of the finest footwear makers not just in Britain but worldwide.
The Declan Chelsea boot is a testament to Grenson’s quality and craftsmanship. If you want a pair of Chelsea boots that will last for years to come, Grenson should be at the top of your list. Their boots are made with attention to detail, so you can enjoy their durability and style for years to come.
I like how Grenson combines traditional methods with modern designs, making its footwear timeless and current. Buying a pair of Grenson Chelsea boots means you’re not just buying shoes; you’re buying a piece of footwear history that’s elegant and durable.
Clarks Originals
Key Style: Clarkdale Gobi
Clarks Originals is famous for its casual, laid-back silhouettes, such as the desert boot and the Wallabee. But its Chelsea boots deserve just as much attention. With Clarks, you can always expect great value for your money.
The Clarkdale Gobi Chelsea boot is a great example of this: durability, quality construction, and timeless looks for under £100. I like how Clarks Originals can combine affordability with craftsmanship, so their Chelsea boots are a great choice for anyone looking to invest in versatile footwear without breaking the bank.
R.M. Williams
Key Style: Gardener Whole-Cut
Named after its founder, a traveling laborer and bushman who became a millionaire through his leatherwork, R.M. Williams is famous worldwide for making some of the best boots around. Their commitment to quality is evident in their Chelsea boots, and they’re no exception.
The Gardener Whole-Cut Chelsea boot has a smooth, soft leather upper that looks luxurious and feels durable. Sturdy soles for style and function so that these boots can go from bush to boardroom.
Dr. Martens
Key Style: 2976
Chelsea boots can be edgy, and Dr. Martens proves them. Famous for their “DGAF” (Don’t Give A F ) attitude, Dr. Martens puts a bold spin on the traditional Chelsea boot.
The 2976 is a great choice. The brand’s chunky shape subverts the traditional slimness of the Chelsea boot. With various designs to choose from—classic yellow-stitch, patterned, or quilted—there’s something for everyone in the Dr. Martens range.
I like how these boots keep the essence of the Chelsea style but add a bit of personality and fun. They go great with black jeans for a tough and sophisticated look.
Crockett & Jones
Key Style: Chelsea VIII
When it comes to quality footwear, it’s hard to ignore Crockett & Jones, and their Chelsea VIII boot doesn’t disappoint. This classic boot has traditional V-shaped side elastics, which add to its looks and make it easy to wear.
Made from the finest calf leather or suede, the Chelsea VIII is luxurious and sophisticated. The attention to detail in craftsmanship is evident, which is a worthwhile investment for any gentleman. The city rubber soles add grip and durability, allowing them to be worn on various terrains and conditions.
Loake
Key Style: Emsworth
With 150 years of heritage, Loake is famous for its modern take on classic footwear. Their Emsworth Chelsea boots are a great example of this: a beautiful combination of elegance and craftsmanship.
The Emsworth has an elegant profile made from beautiful leather, with Goodyear-welted sole units for durability and longevity. One of the great things about Loake’s Chelsea boots is the variety of lasts they offer, so you can find the perfect fit for your foot.
Celine
Key Style: Hector
What’s a luxury rock ‘n’ roll brand without a great range of ankle boots? Celine Homme, under the creative direction of Hedi Slimane, delivers a punk and glamour combo with the Hector Chelsea boot.
This boot, with pointed toes and Cuban heels, adds an edge to the classic shape. Biker embellishments and shiny calfskin leather make it look great. I like how these boots look with skinny black trousers, a sleek and stylish look that’s modern luxury. If you want to make a statement and go rock ‘n’ roll, Celine’s Hector Chelsea boots are a great choice—high fashion with an edge!
Blundstone
Key Style: #500
If you’re after a Chelsea boot, look no further than Blundstone, an Australian brand that’s been making tough boots since the 1800s. Their Chelsea boots cover a wide range—from safety boots to dress boots—but it’s the ones in the middle that really stand out.
The #500 is a favorite. It’s built on strong sole units for added comfort and shock absorption. This solid design is durable and looks great with denim and workwear.
