The Best Men’s Chelsea Boots To Wear This Fall
Pictured Above: Astorflex Bitflex Chelsea Boots
Is there a boot silhouette that can take on so many different forms and capture different vibes quite like the classic Chelsea boot? At once a staple of classic style, worn by rockers for decades, today’s Chelsea boots can lean more rugged (worn-in leather or suede), or just as sharp and dressy as you’d like. And our list of the best men’s Chelsea boots will cover all those bases — just you wait.
The Chelsea boot is a sleek, sharp addition to any man’s footwear rotation, up there with the lace-up work boot or durable hiking boots as an essential for the chillier parts of the year. Chelsea boots can dress up slim blue denim and a striped henley, and they can stylishly complement a richly textured fall blazer or worsted wool suit — it’s all on the table. If you haven’t given the style a shot yet, the below list of the best men’s Chelsea boots is one way to get acquainted with what could become a go-to pair of fall boots.
Astorflex Bitflex Chelsea Boots
From suede chukkas to surprisingly durable lace-up boots, Astorflex takes a careful, nuanced and sustainable approach to its craft. The brand’s Bitflex Chelsea Boot is no different — it’s a particularly versatile and sharp Chelsea boot to buy if you’re just dipping your toes into the market. Made in Italy by a sixth-generation family business and done up with excellent construction, they’re a prime choice.
Plus, they’re available for a relatively affordable price; the Bitflex Chelsea would pair especially well with black denim and an indigo denim jacket — plus your favorite white henley.
“Very comfortable, I wear them for casual and dress, looks great. I get random compliments.” – Blake N.
Price: $250
Beckett Simonon Preston Chelsea Boots
Sharp, stylish, and, best of all, made to order. All of Beckett Simonon’s boots are custom-made and handcrafted by master artisans, and the result is top-notch quality and long-lasting durability. The full grain leather used for the Preston Chelsea Boots is rugged and will last for years to come, developing a gorgeous patina the more you wear it. The interior Vachetta leather lining not only provides solid grip for your feet, but prevents odors, sweat, and excess body heat from ruining your walk.
Thanks to the rounded toe box, the boots look and feel relaxed, great for a stroll down the boardwalk or a boardroom meeting. The leather-lined insoles will mould to the shape of your feet and offer excellent cushioning, with the feel of a custom footbed. With the insole-set steel shank for stability, the SBR rubber heel caps for traction, and the hand-applied shea butter and carnauba wax finish for maximum beauty, these are made to be your ideal everyday boots.
“They are beautiful and well built. I can’t believe the fit and comfort right out of the box. It’s as if they were custom made for me.” – David G.
Price: $400 $259
Allen Edmonds Liverpool Chelsea Dress Boots
Splurge a bit and give your feet the gift of comfort, luxury, and style. The Allen Edmonds Liverpool Chelsea Dress Boots are built to match with slacks or a full suit, the ideal pair of formal boots to slide on when you’ve got a wedding, convention, or a business meeting where you want to look your absolute best.
Each pair is handcrafted in the USA using premium European calfskin for the uppers, vegetable-tanned leather for the soles, and sturdy, supportive CustomCork for the insoles. The 360-degree bench welt ensures these boots will last for years of daily use, and makes them easy to resole or recraft when they start to wear out. You’ll love how sophisticated and streamlined the boots look, the ideal footwear to pair with formal and professional outfits.
“Great boots, very comfortable. Dainite sole is worth every single penny.” – Buuzy, Verified Purchaser
Price $495
Frye Dylan Chelsea Boot
Looking for the perfect boot to take you from work to the bar and back home again in style and comfort? The Frye Dylan Chelsea Boot was built to do exactly that! For those days when you’re out and about, you’ll appreciate the traction and flexibility provided by the rubber outsole, as well as the integrated support of the leather footbed.
The round toe gives your feet room to flex and move as you work or walk, and the six-inch shaft height makes it easy to slide these on and off throughout the day. With a wide range of leather finishes to choose from—including pebble grain embossed, waxed suede, and Cubano leather—you can choose the boots that suit your life and style best.
Price: $398 $278
Ariat Bench Made Younger Western Boot
Show off your cowboy style with the Ariat Bench Made Younger Western Boot. There’s so much I (Andy) love about these boots: the roomy square toe box (to fit my thick feet), the All-Day Cushioning insole for extra support for my oversized (6’6”, 250 lbs.) frame, and the cork-filled forefoot to stave off foot fatigue. Every pair of these Ariat boots is handcrafted from the finest Bison leather sourced in the U.S. and assembled in Leon, the “leatherworking capital of Mexico”, using centuries-old methods that have made Mexican boots some of the finest and sturdiest in the world.
The Chelsea style and low profile makes them perfect for wearing beneath my favorite boot-cut or straight-cut jeans. They’re both handsome enough to serve as my going out boots and sturdy enough to stand up to daily work. Best of all, each pair is utterly unique thanks to the hand-selected sections of leather used in their construction. This is a pair of Chelsea boots I’ll proudly wear all day, every day.
“Very comfortable, easy to break in, and they look great.” – Jdguy
Price: $250
Nisolo Marco Everyday Chelsea Boot
Nisolo Marco builds its Everyday Chelsea Boot to be the ideal companion for busy professionals who need shoes that can keep up with their fast-paced life and work. The combination of a slip-proof rubber sole, cushioned memory foam insole, and water-resistant leather upper ensures you can wear these boots out into rain, slush, or even snow and for hours at a time without wet or tired feet.
The design blends modern styles with classic sophistication, and the result is a sleek pair of boots that match with everything from chinos to slacks to jeans. If you’re all about sustainability and fair trade, you’ll be glad to know the boots are Leather Working Group certified, the workers who build them are paid a fair Individual Living Wage, and Nisolo Marco offsets 100% of the carbon emissions resulting from the production of these boots.
“Great Chelsea Boot! You can feel the leather, and you can smell it too. Very classy and comfy.” – Luis C.
Price: $268
Red Wing Weekender Chelsea Boot
If you’re all about comfort over looks, the Red Wing Weekender Chelsea is the boot for you. I’ll be honest: these boots lack the sleek, refined elegance of many others on our list. The combination of the Chelsea style with the wedge-style sole makes for a slightly clunky look. But once you slip them on your feet and experience how comfortable they are, you’ll find the look doesn’t matter at all. The pull-on style, light weight, flexible construction, and ultra-supportive design makes them the perfect boots to walk around in on your days off when you just can’t be bothered to dress up.
The signature Red Wing copper-colored nubuck leather is gorgeous and will only grow more so as it develops its unique patina. Take these out to walk the dog, strolling around town, or exploring the halls of your local convention center, and you won’t be unable to resist falling in love with them.
“These boots are the best I ever had. They are easy to put on, comfortable to wear and work well even in rainy or snowy conditions. The more you wear them the better they look. I have a wide foot and they fit me perfectly. This is my third winter with these boots and they look great, with no signs of wear on the soles or the elastic panels. By the way, the loops make it super easy to slip these boots on.” – SeanF
Price: $260
Amberjack The Chelsea Boots
How about a pair of Chelsea boots you can take both to work and out for a hike? That’s exactly what Amberjack had in mind when building The Chelsea Boots. Think of them as business on the top, athletic on the bottom—the A-grade, full-grain leather upper and Chelsea style is excellent for days at the office or meetings in town, but the dual-density TPU outsole, slip-resistant tread, and heat-activated foam insole offer all the support, cushioning, and traction you need to hit your favorite hiking trails.
The buttery-soft sheepskin lining maximizes airflow on hot days and keeps your feet comfortable even after long hours of walking or trekking. Dress them up or down; however you wear them, they get the job done in style and comfort.
“These boots are so great! I can’t love them more. I feel like my feet have finally found a home. Seriously, these boots are just heaven. I am buying new jeans and other pieces just so I can always coordinate with these boots. They are absolutely the bomb! Just take a leap and buy them. They may just change your life.” – Paul J.
Price: $199
Rhodes Blake Chelsea Boot
What happens when you combine the classic, comfortable Chelsea boot style with worn-in, vintage-looking leather? You get the Rhodes Blake Chelsea Boot, the perfect boots for your rough and tumble lifestyle. The iconic Chelsea silhouette has been given an upgrade to maximize both durability and the rugged good looks, but don’t think for a moment it sacrificed comfort for sturdiness.
The boots are built using a tumbled leather that feels soft right out of the box, with virtually no break-in required. The waxy leather shrugs off damp and dirt, but develops a lovely patina the more you wear it out and about. The welt construction ensures these boots will last for years without showing wear and tear, but can easily be resoled and repaired as needed. Crafted in the “leather capital of Mexico”, these boots are the ideal choice for any “man’s man”.
“These boots were comfortable out of the box and easy on and off!” – Will C.
Price: $220
Tecovas The Chance Chelsea Boots
The Chance Chelsea Boot is one of Tecovas’ most versatile offerings: it’s built with that rugged Western style you love, but comfort and durability that make it as reliable in the city as out on the range. The bovine leather upper is supple and pliable, adapting to your feet with minimal break-in time necessary.
The low profile, sleek construction, and rounded toe make them easy to wear with everything from work pants to dress jeans to slacks, but the “urban” upper is built onto a reliable Western stacked leather sole (with a rubber end cap) that makes them ideal for everything from ranching to farming. The combination of cowboy spirit and modern durability makes them a pair you can wear anywhere, anytime.
“This is my 4th pair of Tecovas. Wanted something with a lower top for dress wear. The Chance was perfect. All of my other purchases were on line but visited a Tecovas store for this one. The service was excellent as was the inventory they had on hand. You can’t go wrong with Tecovas.” – Donald G.
Price: $295
Danner Bull Run 6″ Wedge Chelsea Boot
For bigger, heavier guys (like me) who need a bit more support and cushioning, I recommend the Danner Bull Run 6″ Wedge Chelsea Boot. The thick polyurethane wedge sole is already amazing supportive and offers excellent stability, but it’s paired with a removable OrthoLite footbed to double down on the cushioning. Wear these over a long work shift or day on your feet, and you’ll hardly notice they’re there.
The mesh liner makes them beautifully breathable so your feet won’t overheat or get too sweaty. The oiled leather upper is water-resistant and will require far less maintenance than most of the boots in your closet. For those who want to use these bad boys on a job site, you’ll be glad to know they’re Electrical Hazard Certified. Sturdy, comfortable, and reliable: what more could you ask for in a pair of boots?
“Awesome boot. No break in time as they are comfortable right out of the box. Easy on and off also.” – Jeff C.
Price: $230
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