The 18 best Chelsea Boots for Men

The Chelsea Boot is a European trend that first became popular all the way back in 1851. It’s a boot, but far more like a shoe. It’s a low-cut dressy boot that has only one real defining characteristic and everything else is considered fair game. The Chelsea Boot has a band of elastic material on the side that gives them a comfortable and secure fit that will move with you. It turned out to be a perfect idea because it has endured generation after generation of style trends that have come and gone. The Chelsea Boot is still here. That’s truly unheard of when it comes to fashion. Some popular styles may see a reboot, but this one might be referred to as a wardrobe staple for men.

The boot can come in any color, with many variations in the height of the heel. You may wear these in the office, out on a date, for a casual night, or at a dress event. They fit right in with a suit, nice denim with a jacket, and even for a night out at the club. They can be comfortable for dancing and suitable for the office all day. The Chelsea Boot has seen a lot of minor style changes over the one-hundred, sixty-eight years they have been in production but they are still basically the same shoe.

Here are the Best Chelsea Boots for men this year.

Urban Outfitters Dress ChelseaUrban Outfitters Dress Chelsea

This boot is perfectly stated simplicity. In soft, brown suede this boot takes on the look of rugged while remaining refined enough to be worn as a dress shoe on the weekend or at the office all week. This supple boot has a pull-tab to help put them on with ease and the heel is a stacked heel that shows the beautiful layers of wood that gives it the luxurious look of a far more expensive boot. For under $100, this is a boot that any man would love to add to his wardrobe.

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Doc Martens 2976 Yellow Stitch ChelseaDoc Martens 2976 Yellow Stitch Chelsea

This boot has the Doc Martens look down pat. It’s a big, thick-soled boot that could easily be a work boot worn under canvas pants. It’s also a great casual boot for the weekends in jeans. With the look and reputation of Doc Martens, you know that they will last forever and since Chelsea Boots have remained in style over one-hundred-fifty years, there’s a good chance that they will still be in style when you pull them out in ten years.

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Church’s Amberely R ChelseaChurch’s Amberely R Chelsea

Everything about this boot screams ‘top of the line’ and you’ll be impressed with the handmade quality. Each boot is handwritten on the inside with the shoe information, by the person who made your shoes. In a rich dark brown that reminds you of a chocolate bar, this boot is suitable for dressier occasions. Well-constructed with a diamond sole, you’ll be comfortable in these in any type of weather.

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H&M Chelsea BootH&M Chelsea Boot

This is a fantastic boot at a fantastic price for the quality that you receive. H&M is a fashion behemoth and they are producing this amazing boot, with shockingly great looks for well under a hundred dollars. In fact, you’ll spend only about half of that price and you’ll have a traditional Chelsea Boot with an understated look and the feel of luxury. It’s cloth-lined and subtle. Available in three colors.

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Allen Edmunds Nomad Chelsea BootsAllen Edmunds Nomad Chelsea Boots

Sporting 360-degree feather welt, these are lightweight, equating with comfort. This boot has a removable insole and they are made in the USA. With a classic look, the Nomad is made from suede, making it perfect for a casual dress party as well as date night on the town.

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Party Men’s Casual Chelsea BootParty Men’s Casual Chelsea Boot

This is a perfect choice for the guy who is just looking to try his first pair of Chelsea Boots and wants to do it on a tight budget. Perhaps you’re a college guy who is concerned about looking good and being on the edge when it comes to fashion trends? Still, you’re in college and money is tight. This is a fantastic-looking shoe at an even nicer price.

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Deer Stags RocklandDeer Stags Rockland

Clean lines, high sheen and exudes class. The Rockland, made by Deer Stag, is a class, Chelsea Boot with the look of style that can be worn on special occasions as well as casual get-togethers. It’s a very affordable boot with a style that is certain to get second looks and impress.

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Sonoma Murray Chelsea BootsSonoma Murray Chelsea Boots

Beautiful boot in leather, with a polyester midsole, the Murray is affordable without compromising the looks of a classic shoe. It goes with everything but it is available in five different colors to suit your wardrobe perfectly. With a foam midsole and a rubber outer sole, they are comfortable and suitable for any walking surfaces you’ll find yourself on.

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Red Wing Heritage Weekender Chelsea BootRed Wing Heritage Weekender Chelsea Boot

It’s a beautiful boot designed with the weekend warrior in mind. It’s perfectly suited to hanging out with friends and watching the game or going out to a pub with your girl. It’s a USA made shoe with tanned leather from the USA. The leather is water, stain, and perspiration resistant. This is a Chelsea Boot that you can sink your feet into and will remain a mainstay of your wardrobe for years into the future. You’ll be hard-pressed to find a better looking casual boot.

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Calvin Klein Rusty Chelsea BootCalvin Klein Rusty Chelsea Boot

It’s a calf suede upper designed boot, making it soft and supple. It will feel like you’ve already worn it from the moment that you put it on your foot. Rare is the boot that you don’t need to break-in. This is a moderately priced Calvin Klein boot but it does not hold back in style. With a stacked heel and very rugged sole, this is a boot you’ll choose over other shoes in your arsenal time and time again.

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Polo Ralph Lauren Talan Chelsea BootsPolo Ralph Lauren Talan Chelsea Boots

Handcrafted burnished full-grain calfskin, these are stylish and sleek. Taking their design to the historical roots of the Chelsea Boot, the Talan is European in every classic way. The foam insole is ergonomic so that you’ll be comfortable and when you start receiving compliments, you’ll never want to take these boots off.

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Carlos by Carlos SantanaCarlos by Carlos Santana

This boot is designed with the signature style of the rock star guitarist Carlos Santana. With the unique dark edging that produces a very bold and stylish look, these boots also sport a bit of metal hardware as well. This will turn heads and be the flash that stands out in the room. If you are not comfortable with attention, don’t wear these because you’ll be treated like a star when you do.

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Thursday Boot Company CavalierThursday Boot Company Cavalier

This boot is a rich chocolate color that will make your mouth water and your eyes glimmer when you gaze upon them. Also available in black or shadow gray, this is a refined boot made from full-grain leather. It will endure wearing in many different climates and situations. Your feet will stay warm, dry, and comfortable while you remain one of the best-dressed in your vicinity.

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Madden M-Gray Chelsea BootMadden M-Gray Chelsea Boot

Budget-conscious boots, made from synthetic materials but they don’t give away the style. Available in five colors that can all be worn for any occasion as you see fit, they make an excellent choice to add to your wardrobe.

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Timberland Men's Larchmont Chelsea Leather BootsTimberland Men’s Larchmont Chelsea Leather Boots

Typical Timberland quality has gone into these rugged, yet refined-looking boots. You can wear these to work all day or you could put them on for some shopping at the mall. Wear them to any social function and you’ll look stylish, trendy, and like a man’s man. 100% leather with a recycled lining and a rubber sole, this boot is up for whatever you want to throw at it.

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Frye Jackson Chelsea BootsFrye Jackson Chelsea Boots

The Jackson Chelsea Boot captures the style of the modern era while keeping with the traditional lines of the Chelsea boot. The mesh interior makes it breathable, so you’ll be able to wear it for hours in total comfort. The look and feel of this boot is simply magnificent.

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Ted Baker Travic Chelsea BootTed Baker Travic Chelsea Boot

This fashion statement is off the charts. The Travic Chelsea Boot will have others asking your for fashion advice or shoe advice, at the very least. People will want to know where you got these because they will make you look like the office manager and the talk of the party. Words such as ‘dapper’ might be through around, so be careful.

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Carl Suede Belted Chelsea BootCarl Suede Belted Chelsea Boot

It moves slightly away from tradition with the belted look, but what a bold statement this makes. It lends a more casual look to the suede boots that will go nicely with jeans, both new or worn. This is a pair of boots that you can wear to your favorite coffee shop and enjoy open mic night, or wear to class. They are light in color, giving them a casual appearance, but they are very well made and eye-catching, thanks to the addition of the playful belt that Carl has added.

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Chelsea Boots

There are some very expensive boots that made our list, as well as some very affordable boots for any budget. Remember that style and function are not always dictated by dollar amount. Choose the boots that feel right for your feet.

With colors of all sorts and designs that play a bit with the traditional Chelsea Boot look, there is a style out there that is calling your name and will be the perfect boot to suit your needs, whether you need a casual boot or a dress boot, Chelsea Boots will have you covered.

You can also find boots that are made vegan friendly, if this is important to you and at least one style has been included on this list. Synthetic materials harm no animals in their making. While leather is a tradition, and generally wears the longest, you can find Chelsea Boots in a number of materials and colors now.