I remember standing in a Banana Republic one day, staring at a pair of Chelsea boots up on the wall.
I turned to my wife and said, “I don’t know if I’m ready.”
She looked at me. “What does that even mean?”
See, I’d never owned a pair of Chelsea’s before—I was stuck on the cap toe lace up boot style. I wasn’t sure I was ready to step my style game up.
“Quit being an idiot,” she said, gently. “Get the boots already and let’s go.” Ah, I remember the twinkle in her eye.
Well, I got the boots.
And I’ve been wearing Chelsea boots probably four to five days a week ever since.
In my humble opinion, they’re the best shoe a guy can wear. You can find a sleek dressy pair that works well with a suit, or you can get a rounded toe version that pairs like a charm with all things casual.
Really, it’s hard to go wrong with a Chelsea boot. They’re sophisticated and masculine. They make a t-shirt and jeans combo look classy. What’s not to love?
In honor of my favorite boot, I put together a list of the five best Chelsea boots out there right now.
Warning: if you’re not ready to catch the Chelsea boot fever, stop reading now.
My Recommendations
Most Comfortable: Amberjack The Chelsea
In their own words, Amberjack has made “…the world’s most advanced dress-casual shoes” and The Chelsea sticks very closely to that vain.
Although these boots don’t massage your feet or let you hover like you might expect from the world’s most advanced dress-casual shoes, they’ve made some serious advancements when it comes to balancing comfort and style.
Usually you can’t have both, but Amberjack puts a strong foot forward (pun intended) with The Chelsea and its dual-density outsole.The heel is made with tough, hiking boot material, but also features a recessed center portion that improves cushioning.
The midsole features a high-performance, athletic material that allows the shoe to flex and feel like a sneaker around the ball of your foot. Together, the heel and midsole make for a supportive and bendy shoe that won’t make your feet tired any time soon.
The inner lining is made from A-grade, premium buck skin leather that’s laser-perforated to improve airflow.
What I Like
- The Chelsea keeps the sleek profile of classic Chelsea boots while having comfort-enhancing add-ins.
- Its dual-density outsole makes for all-day comfort and the perfect balance between support and sneaker-like flexibility.
- The perforated leather lining helps keep your feet cool, even in a boot.
What I Don’t Like
- The leather overlay panel on the top and front of the boot makes The Chelsea slightly less formal.
What Other Reviewers Say
I had trouble finding a review that didn’t have some version of, “These are the most comfortable shoes I’ve ever owned”, so it’s safe to say that The Chelsea is a hit. Happy customers also loved the sleek style and colorway options.
Of the very few negative reviews I could find, several mentioned delayed shipping times or issues with order fulfilment. However, Amberjack commented on each of these negative reviews and looked to have resolved the issue with each customer.
The Verdict
There’s stiff competition in the battle for the most comfortable Chelsea boot, but Amberback has our pick due to their seamless combination of comfort and style.
If you’re in need of a new Chelsea boot that will look slick, provide ample support, and wear like a sneaker, check out Amberjack’s The Chelsea.
Style meets supreme comfort with these Chelseas. A dual-density outsole gives needed support and flexibility at the same time to keep these comfy all day long, and a perforated inner lining helps keep your feet cool and dry.
Best on a Budget: New Republic Sonoma Suede Chelsea
Suede Chelsea boots bring a good balance or formal and casual style to any outfit, and my favorite suede Chelseas on a budget are the New Republic Sonomas.
New Republic offers a wide variety of classic, timeless footwear with modern updates at remarkably affordable prices. Their goal is to provide timeless fashion to everyone, and they’re handily accomplishing this with quality suede Chelsea boots typically priced at $100.
The Sonomas feature 100% genuine suede uppers and a soft, split leather lining. The collar is fairly high on these, which I actually prefer since there’s less chance of your socks peeking out from behind cuffed pants.
The outsole is made with full-length, natural crepe, which is a style of rubber shoe sole, not the thin French pancake. Crepe soles are bouncy and feel like sneakers, which makes the Sonomas particularly comfortable.
What I Like
- Typically priced at $100 from frequent sales, it’s hard to find a cheaper Chelsea boot at this level of quality.
- The premium construction materials go a long way in making these boots comfortable and durable.
- The crepe sole is responsive, comfortable, and provides good traction.
What I Don’t Like
- They’re only offered in suede, not smooth leathers.
What Other Reviewers Say
The majority of reviews for the Sonomas are positive, with happy customers talking about how much they like the style, quality construction materials, and affordable price point.
Of the few negative reviews I found, several guys said the boots were narrow and not too comfortable, but these reviews were in the minority by a long shot.
The Verdict
It can be tough to find an affordable Chelsea boot that doesn’t look cheap and is built for quality, but New Republic delivers with the well-priced Sonoma.
If you’re on a budget but want to rock some suede Chelsea’s, check out New Republic’s Sonomas.
Great Value: Beckett Simonon Bolton
While most Chelsea boot manufacturers create their boots in bulk and then let them sit in warehouses and on shelves until they’re potentially sold, Beckett Simonon took a radically different approach and decided to only make shoes when they had orders to fulfill.
It’s an odd approach in the fast-paced and competitive shoe industry, but it allows their master artisans to take their time with every shoe and ensure premium, long-lasting quality.
The Bolton Chelsea takes all the classic attributes of a quality Chelsea boot and enhances them, while still keeping an affordable price point.
Full-grain leather uppers, Vachetta leather linings, blake stitching, and SBR rubber heel caps make for a luxurious, supportive boot, and an almond-shaped toe box gives a refined, contemporary look to the silhouette.
Best of all, Beckett Simonon has taken measured steps to ensure that it’s working with master artisans in responsible and ethical working conditions.
By cutting out the middlemen, unsold inventory, and high markups, Beckett Simonon is able to offer premium footwear at a significant discount, and the Bolton Chelseas are no exception.
What I Like
- The Bolton Chelseas are hand-crafted by master artisans in sustainable, ethical working conditions.
- The almond-shaped toe box gives a subtle, unique, and refined look to these Chelsea’s.
- Premium leathers are used for the uppers and interior lining, and blake-stitched construction lets these boots be easily re-soled.
What I Don’t Like
- Since the boots are made to order, it can take roughly 6 weeks to receive your order. However, they offer free shipping in the US, a 60-day money back guarantee, and a 1-year warranty.
What Other Reviewers Say
The Bolton Chelseas have rave reviews. Many noted the exceptional quality and beautiful construction, as well as the premium construction materials and perfect fit of each pair.
These boots actually don’t have negative reviews. The lowest review (4 stars) wished for slightly more cushioning and support in the heel.
The Verdict
Beckett Simonon’s radical approach to quality footwear is paying off. The Bolton Chelseas are well-loved for their premium materials, quality construction, and impeccable details.
If you’re in the market for this men’s footwear classic and don’t mind waiting a bit for quality, I recommend Beckett Simonon’s Bolton Chelsea Boots.
For made-to-order, hand-crafted quality at a fraction of the cost, look no further than Beckett Simonon’s Bolton Chelseas. Premium construction materials and an almond-shaped toe box elevate these boots above the vast majority of the competition.
Best Chelsea Boots for Walking: MYRQVIST Elfvik
One of the many reasons I love Chelsea boots so much is their ability to quickly slip them on and head out the door. And I don’t know of another boot that handles as well as an errand-runner as MYRQVIST’s Elfvik Chelsea.
It’s the small rugged details that makes this boot stand out—a Vibram commando sole and storm welt gives it a confident, almost aggressive silhouette that is perfectly suited to casual wear.
These boots have Goodyear welt construction, which is a premium method of shoe construction known for its durability, water-resistant properties, and how easy it is to re-sole.
They’ are also’re built with water repellent Charles F. Stead waxed suede, lined with a padded insole, cork filling, and sit on a sturdy Vibram outsole which all combine for all-day walking comfort.
What I Like
- The boot’s profile and build is distinctive, confident, and perfectly suited for running errands and long walks.
- Handcrafted in Portugal from premium water repellent waxed suede which feels fantastic and will hold up when the weather turns on you.
- The Goodyear welt construction and Vibram commando sole combine for a seriously durable shoe.
What I Don’t Like
These are only really suited for casual wear which means they lack some versatility.
What Other Reviewers Say
Reviewers overwhelmingly trend positive for these Chelsea boots. Many satisfied reviewers loved the construction quality and durability, as well as the rugged style.
A few guys complained about slow shipping times, but MYRQVIST’s customer service were seemingly onto it with replies to each mention.
The Verdict
MYRQVIST took a classic style and vamped it up slightly to have a confident, aggressive silhouette. With premium waterproof leathers throughout, Goodyear welt construction, and hand-crafted details, the MYRQVIST Elfviks are best-in-class errand-running Chelseas.
MYRQVIST took a classic style and vamped it up slightly to have a confident, aggressive silhouette. With premium waterproof leathers throughout, Goodyear welt construction, and hand-crafted details, the MYRQVIST Elfviks are best-in-class errand-running Chelseas.
Best for Winter: Velasca Bagaj
Unless you’re rocking a pair of Blundstone’s, which are usually casual, it’s hard to find a pair of Chelsea boots that are appropriate for the winter months and the bad weather that usually comes with them.
Velasca, an Italian footwear brand that cut out the middlemen to sell directly to the consumer, looks to solve this issue with their winter-capable boot, the Bagaj.
Constructed with smooth, full-grain calf leather and a classic Blake stitch, the upper portion of these boots look like your typical Chelsea. However, the outsole is where these get winter-ready.
These boots are made with a Trento winter Vibram lug sole, which is about as hefty as a work boot sole. These soles are well-equipped for dealing with the slippery, wet conditions of winter, especially since Vibram is well-known for their sturdy hiking soles.
What I Like
- The Trento winter Vibram lug sole is rugged, resilient, and ready to take on winter conditions.
- The Bagaj is made with premium materials throughout, with full-grain leather uppers and calf leather lining.
- The Blake stitch construction helps with durability and makes it easy to re-sole these if need be.
What I Don’t Like
- Compared to some other winter boot options, these will be tough to afford if you’re operating on a budget.
What Other Reviewers Say
These boots don’t have too many reviews, but the ones I found had good things to say about the construction quality, durability, and grip of the outsoles. One reviewer who had good things to say about the grip and stability of these was from Norway, and I can imagine he has ample use cases for a good pair of winter boots.
I couldn’t find any negative reviews for these boots, which is certainly promising.
The Verdict
Velasca brought a quality Chelsea boot to the table with Blake stitching and full-grain leather, and elevated it into a sturdy, winter-ready Chelsea with a thick, Vibram lug sole.
If you want a high-quality pair of Chelseas that will keep you warm and slip-free in the winter, I recommend Velasca’s Bagaj Chelsea.
This well-constructed, quality Chelsea boot is ready for winter with its hefty Vibram lug sole. Form and function combine here, for when you want to be slip-free in winter conditions but still stylish.
Best Black Chelsea Boots: Ace Marks Troy
Ace Marks does direct-to-consumer Italian leather dress shoes and their Troy is our top pick for a dress Chelsea.
Outfitted with a leather sole and lightweight vegetable tanned Italian calfskin leather, these make a statement.
Of all the boots on this list, the Troy from Ace Marks is the sleekest and most narrow.
What I Like
The quality is outstanding—veg-tanned calfskin leather boots feel outstanding.
I like how sleek and slim these boots are.
There are a few classy color options available, though I recommend staying in the darker, more dressy range.
What I Don’t Like
The Troy is quite narrow which can be an issue for folks with wider feet.
What Other Reviewers Think
The Ace Marks Troy has racked up over 20 reviews on their website, with most reviewers praising the slim silhouette. Ironically, this is where the few complaints come from, too. This is a narrow dress Chelsea, so if you have especially wide feet, Ace Marks EE size might not feel comfortable at first.
The Verdict
For a high-end dress Chelsea, the Ace Marks Troy is a fantastic value. These Blake stitched, Italian calfskin leather boots look and feel beautiful, and their slim profile is versatile and works just as well with a suit as it does jeans.
The Ace Marks Troy Chelsea Boot is made with premium Italian calf-skin leather and a Blake stitched construction. It's lightweight, creamy-smooth, and has a stunning profile.
What Are Chelsea Boots?
Chelsea boots are traditionally slim, form-fitting ankle boots with gored elastic sides. They don’t have laces and are easy to slip on and off.
They became wildly popular back in the ‘60s as bands like The Beatles and The Rolling Stones were seen wearing them often.
But while bowl cuts are a thing of the past, the Chelsea boots remains popular.
A lot of guys (myself included) love the style because it pairs well in a huge variety of outfits. Boxier style Chelsea’s, like those from Amberjack, look fantastic under jeans and chinos. Dressier styles, like those from Beckett Simonon will pop with a suit or under more formal trousers.
In any case, Chelsea boots are an excellent way to elevate your casual style. As I said earlier, they can make jeans and a t-shirt look like an outfit masterpiece.
Originally, these boots were all made with leather soles, but over time, more modern updates became available.
Personally, I wear Chelsea boots too often to stick with the leather sole. I prefer a full rubber sole, or at least a rubber and leather hybrid. You’ll see that preference throughout the list, too, so keep that in mind as you peruse your options.
I take good care of my shoes, but I do a lot of pavement pounding and my shoes have a limited lifespan because of it. For me, rubber soled shoes are a better investment (unless I’m shopping for a formal occasion. In that case, a leather sole is the better choice).
My Dad is a builder and I got these for him after he kept complaining to me that all his socks gave him blisters and sweated up his feet. The good news? He loves them and now he won't stop talking about socks. The bad news? Now he won't stop talking about socks.
3 Things to Consider When Buying Chelsea Boots
1. What’s the Occasion?
I always buy my shoes based on what sort of occasion I’m looking to dress for. For instance, I’ll ask myself: do I want a pair of shoes that are more casual, but I can pair with a suit? In that case, I’d look for a slimmer profiled boot.
Or: did I just get a new bomber jacket that looks awesome with a pair of jeans but needs something sleek to bring the outfit together? A relaxed, durable Chelsea might be the trick.
A slightly boxier style like Moral Code’s Lawry is my top-choice if you’re looking to fill out your casual shoe rack. While I love them for their ability to elevate a pair of jeans, they’re not the best look when paired with a suit.
For that, I’d choose a slimmer, more European style Chelsea boot.
2. How’s the Leather?
With most Chelsea boots, there’s no brogue pattern, no cap-toe—nothing to hide behind. If the shoe isn’t made with high-quality leather, it can lose its shape quickly and cease to give you that effortless elegance.
I can vouch for the selections on this list (yep, even the budget pick). None of these choices will do that toe indent thing that looks floppy and terrible. You know what I’m talking about.
3. Will It Last?
If there’s one thing I’ve learned over the past 10 years, it’s that there’s no point in buying cheap clothes that don’t last. When I was in my early 20’s, I’d buy the cheapest stuff I could get away with and still look good.
The problem is, after you wash your clothes or go for a long walk in your shoes, it looks terrible.
I remember the last cheap pair of boots I bought. I stood in a hot parking lot in LA and literally watched my shoes change shape. They were never the same. And I never bought cheap again.
Don’t be afraid to put some cash on the table here. Good leather boots are an investment. And if you care for them well, they’ll last you for many fashionable years.
How to Wear Chelsea Boots
Learn about the two styles of Chelsea boots and how to wear them in our special fashion tip video below:
When Life Gives You Chelseas
Across these six Chelsea boot options, you shouldn’t have any issues finding the right pair for you.
Our top recommendation for those who want all day comfort and the style of a Chelsea boot is Amberjacks’s The Chelsea.
Style meets supreme comfort with these Chelseas. A dual-density outsole gives needed support and flexibility at the same time to keep these comfy all day long, and a perforated inner lining helps keep your feet cool and dry.
If you’re in the market for a hand-made, made-to-order, refined option, check out Beckett Simonon’s Bolton Chelsea.
I recommend MYRQVIST’s Elfvik if you’re after a premium boot ideal for casual wear and errand-running.
If you’re on a budget, you can’t go wrong with New Republic’s Sonoma Suede Chelsea.
After a lot of wear, I’ve concluded that the New Republic Sonoma nails the shoe trifecta of classic style, affordable pricing, and quality construction. I’m a fan.
Lastly, if you need a sturdy, capable Chelsea for the winter months, I recommend Velasca’s Bagaj Chelsea.
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