9 Best Dress Boots for Men in 2022: Stylish and Timeless

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by  William Barton | Last Updated: 

It’s time for a new pair of dress boots, but the last pair you got fell apart too quickly and gave you nothing but blisters in the process. It’s a problem we’ve all faced.

In this guide, I’ve handpicked the best dress boots for men so you can find a pair that looks rich, feels comfortable, and ticks all the boxes for that big event you have coming up.

Best Overall
  • Exquisite Italian full grain calfskin leather
  • Oxford-style boot with broguing on toe-cap
  • Excellent durability, comfort, and quality
Runner Up
  • Goodyear welted construction, which is unique for a dress boot
  • Ornate wingtip broguing pattern across the entire upper
  • Rubber studded soles for excellent shock absorption and traction
Best Chelsea
  • Box calf leather creases gently and looks fantastic for a long, long time
  • Sleek, stylish shape that works with more formal outfits
  • Semi-square tip has a rich and cosmopolitan look
Best Budget Dress Chelsea
  • Only dress boot on this list under $200
  • Goodyear welt with a sleek profile
  • Available in EE/EEE sizes
Most Comfortable
  • True to its name, it’s extremely comfortable
  • Wholecut yearling leather has a tight grain, creases gently, and looks classy
  • Padded heel lining
Best Waterproof
  • 360 degree Goodyear Storm welt with a waterproof membrane in the lining
  • Dainite sole has excellent traction on wet surfaces
  • Available in a massive variety of sizes, from AAA width to EEE widths
Best Winter
  • Tumbled kudu leather is highly weather resistant and has an interesting texture
  • Classy wingtip broguing pattern along the upper
  • Decked out with a heavy Vibram winter lug sole for traction in snow and slush
Best Dress Cowboy
  • Fine full grain calfskin leather with a glove leather lining
  • Leather sole with brass tacks in the arch
  • Classic western style stitching in the toe box
Best Dress Chukka
  • Formal almond shaped toe and leather sole make this acceptable as a dress boot
  • Full grain Italian calfskin leather is soft, supple, and creases gently
  • Classic Blake stitch construction for a lighter weight, lower profile, and greater flexibility

My first pair of dress boots was a total disaster.

They tore my heels up for about three months, and they fell apart not too long afterward. Sure, I spent less than $100, but six months after buying them, I needed to get yet another pair. 

Maybe you’re in a similar position. Sure, you can learn the hard way like I did. Or you can pick one of these amazing dress boots and get the right boot without the trial and error I had to go through.

I didn’t just make this list up: I either own these boots myself, or I own a pair from the brand itself and can speak to the brand’s quality personally. I know you’re going to love one of these pairs of boots.

How Did I Come Up With My List?

I’ve reviewed over 75 boots at the time I’m writing this. I own most of the boots on this list. Some of the boots I don’t personally own, but I own other models from the same brand. 

So for each of these dress boots, I’m recommending them based on my personal experience after spending my own money. 

Over the past four years, I’ve spent hundreds of hours researching different brands. From those hundreds of brands, I’ve tried over 50. And from those 50+ brands, I’ve bought boots from the following seven brands (two brands make my list of best dress boots twice). 

And it’s not just me: the community of 10,000+ boot fanatics over at the BootSpy YouTube channel have also had fantastic experiences with these boots and brands.

9 Best Mens Dress Boots

Best Overall: Beckett Simonon Elliot

1.
Beckett Simonon Elliot Balmoral Boot
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If I could only choose one dress boot, it’d be the Beckett Simonon Elliot

The Elliot is technically considered a Balmoral boot, which is nearly identical in construction to an Oxford shoe, but with a taller shaft, making it a boot. 

In dressy situations, shoes are usually the go-to, and are generally considered more formal. But sometimes a man just wants to wear a boot. I like wearing boots for more formal occasions because when you sit in a suit and the pant leg rides up to reveal more leather, it’s just a great look.

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The Beckett Simonon Elliot is, in my opinion, the best “bang for your buck.” It’s made with fine Italian calf-skin leather, features Blake stitch construction, and it looks incredible. 

There’s one massive downside to ordering with Beckett Simonon, though. They handcraft all their shoes and boots to order, so you’ll likely have to wait several months before they arrive. To me, that’s completely worth it, because this sub-$300 boot has a similar level of quality as some of my $500-$600 boots.

But if you have an event coming up soon, check out my second pick on this list, as that nets you a high quality boot at a similar price, but much quicker. Otherwise, if you have time to spare, the Beckett Simonon Elliot is the best dress boot for your money.

What I Like

  • The Italian vegetable tanned full grain calfskin leather is some of the nicest I’ve seen on a pair of boots.

  • The shape is classy and modern but not so slim that it’s trendy looking. They have a solid and sophisticated presence. 

  • Blake stitch construction means you can resole these should the sole ever wear out.

  • They feature a rubber sole, which I like for added traction, though leather soles technically are the most formal. 

What I Don’t Like

  • Beckett Simonon can take between 6-8 weeks to craft and ship your boots out to you. Expect a hefty wait time.

What Other Reviewers Say

Many reviewers who’ve bought one pair of Beckett Simonons go back and buy at least one more pair. This brand has a loyal and growing following.

For the Elliot specifically, many of the reviewers mention the leather quality—they’re surprised at how thick and supple the leather is.

The Verdict

If you’re looking for a dress boot that works for formal, semi-formal, and even a snazzy casual outfit, the Beckett Simonon Elliot is my top choice. 

The value you get for your money is among the best I’ve ever seen on a boot. Considering the leather quality, comfort, and style of this boot, it competes with boots twice its price. 

But you have to be willing to wait. Because Beckett Simonon boots are handmade to order, they can take several weeks—sometimes even months—before they ship out. 

Beckett Simonon does a great job with communication in the meantime, and they let you know at the time of purchase when you can expect to get your boots. It’s how the brand keeps their prices so low (they don’t have to spend anything on extra stock). Their greatest strength is also their greatest weakness.

If you have time to spare, you’ll love your Beckett Simonon Elliots.

Best Overall
Beckett Simonon Elliot Balmoral Boot
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Runner Up: Thursday Boot Company Wingtip

2.
Thursday Boots Wingtip
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Thursday Boot Company is known for their more rugged, everyday boots. But they have a Wingtip that rarely gets any coverage, but is a stellar deal. 

Before I’d gotten my Beckett Simonon Elliots (my top dress boot), I needed something in the short term for a wedding. So I picked these up because they ship quickly. And I was blown away with the quality.

The Thursday Wingtip has a super slim shape—it’d be tough to manage if you have wide feet, but the profile looks rich.

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There’s extensive broguing details on the toe cap and around the upper, so the Wingtip is one of those boots that easily looks three times what it actually costs. 

It’s made with the industry gold standard Goodyear welt, with a comfortable Poron footbed and a rubber stud sole.

What I Like

  • This boot is very slim and classy looking, and the squared toe is unique.

  • Goodyear welted construction is more rare in a dress boot, and it offers excellent weather resistance and recraftability.

  • The price is excellent considering the leather and build quality.

What I Don’t Like

  • Because they’re narrow, they’re a no-go for guys with wide feet. I have standard width feet, and they can be a bit tiring after a long event like a wedding (granted, there’s a lot of dancing going on). 

What Other Reviewers Say

Many reviewers praise Thursday Boots for their customer service—I’ve never had to return a pair of their boots myself, so it’s helpful to know (and I have ten pairs). 

A lot of reviews online speak about the comfort of these dress boots. That’s the Poron insole chiming in there.

The Verdict

I chose the Thursday Boot Company Wingtip as a runner up for the best dress boot for guys because it’s extremely versatile and it’s probably the dress boot I wear most often. 

Yes, I like the Beckett Simonon Elliot more, and that’s the one I reach for when I need to put on a suit. But because the Thursday Wingtip is super comfortable and has a relatively hefty rubber sole (compared to most dress boots), it’s a fantastic dress boot if you do a lot of walking, or want to wear something classy with a pair of crisp blue jeans. 

And you’re also getting excellent value for money with the Thursday Wingtip. A Goodyear welt constructed boot with high quality leather for under $250? Count me in.

Runner Up
Thursday Boots Wingtip
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Best Chelsea: Carmina Simpson

3.
Carmina Chelsea Boots 80216 Simpson
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You might not know this, but Chelsea boots aren’t really formal boots. But if you want a classy pair of Chelseas that work well in a dressy situation, there’s none better than the Carmina Simpson Chelsea

Carmina handcrafts their boots in Spain, and they have a modern, European style to them. This boot features box-calf leather, which creases and ages gracefully so you can wear these for years and they’ll still look dressy as ever.

What I Like

  • They’re Goodyear welted and have a classic leather sole—this makes this particular Chelsea more acceptable for formal occasions. 

  • Fully lined with calfskin leather. Now that’s fancy. And comfortable.

  • The black box calf leather is incredible: the aniline dye is deep and rich, and the tight grain causes the leather to crease gracefully, so they just look more distinguished with time.

What I Don’t Like

  • Carmina doesn’t offer great sizing information on their boots, nor do they offer much information on the difference between their lasts, but with enough poking around their site, you can usually find out which size is right for you.

What Other Reviewers Say

The Carmina Simpson doesn’t come in the standard “D” width, so a few reviewers were caught off guard when their boots came in more narrow than expected (though Carmina says on their site to go up a half-size). 

Make sure you read what the brand has to say on sizing before picking these up and you’ll count yourself among the dozens of reviewers raving about their new Carminas.

The Verdict

Carmina is considered one of the best dress boot and dress shoe brands in the world, and there’s a good reason for that. 

At over $500, these boots are quite pricey, but the quality is as good as it gets. If you want a dress Chelsea you can wear for a formal occasion, or if you just want a classy Chelsea that hits the upper limit of quality, then I definitely recommend the Carmina Simpson.

Best Chelsea
Carmina Chelsea Boots 80216 Simpson
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Best Budget Dress Chelsea: Thursday Boot Company Cavalier

4.
Thursday Cavalier
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I recently had a friend ask what the best classy black Chelsea was, and I recommend the Carmina and the Thursday Cavalier

He picked the Thursday Cavalier. Why?

Because it’s under $200, and sometimes that’s all we want to spend on a pair of good boots. 

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Many versions of the Thursday Cavalier are in more casual leathers (like any of their WeatherSafe suede choices), but if you get the Cavalier in the full grain black leather, it’s slim and classy enough to pass in a more formal situation.

The Cavalier features a 360-degree Goodyear welt, full glove leather lining, and has a leather sole with rubber studs embedded in it. 

If you’re on a strict budget and can’t cross the $200 mark, the Thursday Cavalier (in black) is the best dress boot option for you.

What I Like

  • A Poron insole makes for a comfortable experience—these are great if you need to walk a lot in them.

  • 2mm full grain leather with a box calf leather lining means these have a lot of leather compared to other dress boot brands. They’re quite substantial and make for great everyday boots, too. 

  • They don’t have a nylon pull tab at the back, which can be more difficult to put on, but there’s no tab to catch the back of your pant leg when wearing a suit or trousers. 

What I Don’t Like

  • The Cavalier tends to “deflate” relatively easily. I recommend getting a pair of cedar shoe trees for yours to help them keep their shape (this is true for any boots you want to keep looking good). 

What Other Reviewers Say

At the time of writing, the Cavalier has racked up over 1,200 reviews averaging to a 4.9 out of 5 stars, which is pretty insane. A lot of reviewers bought them because they can dress them up or down. 

It’s true—they have that slim shape that works well with slim-fit jeans or dress trousers. If you want, check out my in-depth Thursday Cavalier review here.

The Verdict

A good dress boot should look rich. And that can be hard to pull off if you’re shopping with a tight budget. 

If you need to stay under $200, then the Thursday Cavalier in black full grain leather is the best option for you. It has all the hallmarks of a high quality boot, looks classy, and stays relatively affordable.

Best Budget Dress Chelsea
Thursday Cavalier
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Most Comfortable: R.M. Williams Comfort Craftsman

5.
R.M. Williams Comfort Craftsman
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It makes sense that a boot with the word “comfort” in it would win my spot for most comfortable dress boot. 

Well, the R.M. Williams Comfort Craftsman is one of the most comfortable boots I own, period. And it’s a wholecut Chelsea made with Yearling leather. 

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Even if these R.M. Williams boots weren’t all that comfortable, they’re total beauties and would make this list one way or another. It just helps that they have a padded heel counter, a soft insole, and plenty of arch support. 

If I’m going to be on my feet a lot but still need a pair of dress boots, I reach for the R.M. Williams Comfort Craftsman.

What I Like

  • This is a wholecut Chelsea, meaning it’s made from a single piece of leather—it looks unique and sophisticated.

  • The Yearling leather and lining are supple, thick, and high quality.

  • It’s extremely comfortable because of the padded heel counter and excellent arch support.

What I Don’t Like

  • The pull tabs in front and back can catch your trousers. 

  • Aussie sizing has a learning curve for Americans. For these, order a full size smaller than your usual sneaker size.

What Other Reviewers Say

A lot of reviewers noticed that these can feel quite snug at first. However, they noted that the Yearling leather does stretch a bit within the first month or so of wearing, and that eases the snugness.

At that point, the comfort is phenomenal. I’ve had the same experience with mine. There was some crowding of my smaller toes in the first month, but after I put in some miles, they loosened up and are one of the most comfortable pieces of footwear I own now.

The Verdict

The R.M. Williams Comfort Craftsman has some elements to it that are a little more rugged than your average dress boot, but if you take decent care of the leather, it’ll do well in semi-formal and formal outfits. 

But no other dress boot touches the R.M. Williams Comfort Craftsman on the level of comfort. I mean, it’s in the name.

Most Comfortable
R.M. Williams Comfort Craftsman
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Best Waterproof: Allen Edmonds Hamilton Weatherproof Oxford

6.
Allen Edmonds Hamilton
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The Allen Edmonds Hamilton is a unique boot in that it’s a classic dressy style but is completely waterproof. 

It’s an Oxford style boot with plenty of broguing around the upper—you may not like all that flourish, but it’s a fit for officewear. 

The Hamilton stays 100% waterproof because of the weatherproof membrane between the leather upper and lining. It also features a 360-degree Storm welt that’s also sealed.

What I Like

  • This is one of the few dress boots that look good and are genuinely weatherproof.

  • Allen Edmonds offers a massive variety of sizes, from narrow to wide widths. 

  • The Dainite sole offers excellent slip resistance on wet concrete. 

What I Don’t Like

  • There’s no black version available. 

What Other Reviewers Say

Reviewers are impressed with the Allen Edmonds Hamilton. Many use it as their go-to winter dress boot for when you’re not sure if the clouds on the horizon are coming in. 

Allen Edmonds has a reputation for high quality shoes and boots. Many picked up their dress-shoe size and liked the fit, though I recommend going a half-size smaller than you would in your dress shoes.

The Verdict

There are few weatherproof dress boots on the market. If you want to maintain high quality construction and materials, while still getting something 100% waterproof, the Allen Edmonds Hamilton is the best option on the market.

Best Waterproof
Allen Edmonds Hamilton
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Best Winter: Velasca Avocatt

7.
Velasca Avocatt
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Winter where I live typically means rain, slush, mud, and a whole bunch of grumbling whenever I have to leave my apartment. 

That’s why my favorite winter dress boot is the Velasca Avocatt

It’s a Chelsea style brogued wing-tip. This isn’t a very formal boot, but it’s certainly office appropriate. I like the slip on, slip off element of this boot because when I get home out of the ice and slush, I want my boots off as fast as possible. 

Also, the Velasca Avocatt has a Vibram lug sole, which performs really well on ice. 

This boot isn’t as slim and classy as the Allen Edmonds Hamilton, but it’s got more heft, which makes it a better fit for snowy conditions.

What I Like

  • The heavy Vibram lug sole has excellent grip on slush and ice. 

  • The brogued wingtip details make this a fantastic boot for the office. 

  • Because it’s a Chelsea, this boot slips on and slips off easily. 

  • Kudu leather is tough and offers excellent weather resistance. 

What I Don’t Like

  • The sizing options are a bit limited. 

What Other Reviewers Say

Velasca is a relatively unknown brand from Italy (at least here in the US), but my experience with the brand has been nothing but awesome.

The Verdict

For a winterized dress boot, you need a heavy sole. The Velasca Avocatt delivers on this and is a fantastic option for commuters looking for a dress boot that can handle icy and snowy conditions.

Best Winter
Velasca Avocatt
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Best Dress Cowboy: Tecovas Cartwright

Cowboy boots technically aren’t dress boots. You can take the country boy out of the country, but you can’t take the country out of the country boy.

The Tecovas Cartwright is simple, classy, and if you treat it well, it’ll serve as your go-to dress cowboy boot.

I bought my Tecovas Cartwrights after a lot of research, and I landed on them because of the leather quality. It’s going to crease gently, and with a little love and care, it’ll continue to look spiffy after years.

What I Like

  • Tecovas makes their boots in the traditional way, so this boot has a leather sole—classic for a dress boot.

  • There’s a light brown and black version available.

  • The western-style stitch on the upper is simple and understated, but still shows it’s obviously a western boot. 

What I Don’t Like

  • While I like the leather sole, I highly recommend scuffing it up a bit before you take it to any event. If you have to walk on marble or carpet, you’ll look like a newborn deer because it’s so slippery. 

What Other Reviewers Say

The Cartwright takes a little time to break in, especially because the toe is a little more narrow, so you might feel a gentle squeeze at the ball of your foot. I experienced this also, but so long as your feet don’t tingle, the leather will stretch out a bit and you’ll get a comfortable fit.

The Verdict

The Tecovas Cartwright is a classy looking cowboy boot. Sure, it’s technically not a dress boot, but no cowboy boot is. 

Still, if you don’t want to give up your western boots and you have a wedding or big meeting coming up and you want to hit ‘em with some Texas charm, the Cartwright is your best bet.


Best Dress Chukka: Beckett Simonon Ellis

9.
Beckett Simonon Ellis
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Beckett Simonon makes my list twice because they’re just that good. Especially when it comes to dress boots. 

The Ellis is my favorite dress chukka because it’s simple, clean, and the leather is absolutely phenomenal. 

Made with Italian full grain calfskin leather, it’s creamy, soft, and ages gracefully. Plus, these chukkas are super comfortable. 

Again, as with any Beckett Simonon order, you can expect to wait between 1-4 months to actually get your boots because they hand make them to order.

What I Like

  • The leather is top quality and the value for money is among the best in the business.

  • There are five different color options at the time of writing—all acceptable for at least business casual, and the black can even fit in for black-tie level formality. 

  • While the waiting time is long for these, Beckett Simonon does a great job communicating often with you throughout the experience. 

What I Don’t Like

  • The wait time is long. 

What Other Reviewers Say

It’s very common to read from reviewers who pick up one pair, and then quickly buy another two or three pairs as soon as the first pair arrives. Fit and sizing is fairly simple to figure out, though people who’ve bought the wrong size have no trouble with returns.

The Verdict

If you’re looking for a dress chukka, the best value for money I’ve seen is the Beckett Simonon Ellis

There are some expensive chukkas out on the market, and while I still would like to try some of the higher end Alden’s, I’m super happy to get a similar quality at a much less expensive price.

Best Dress Chukka
Beckett Simonon Ellis
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Can You Wear Dress Boots with a Suit?

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Many men only wear dress shoes with their suits, but dress boots are perfectly acceptable to wear with a suit. 

There are only a few occasions where you’d want to stick with shoes, like if you’re attending a formal black-tie or white tie event. In that case, it may be a better option to choose opera pumps or Oxford shoes. 

But how many events have you gone to with that level of formality? I’ll be honest: I haven’t. 

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Most events that call for any sort of formality today usually require a suit—navy and charcoal are the safest bets. In these situations, a pair of dress boots is an outstanding choice. 

I wear dress boots to any wedding I go to. I like that when I sit, the leg of my trousers raises and shows off more of that sweet leather. You can also wear dress boots to any big office presentation or holiday party. 

Dress Up

Having one good pair of dress boots is a must in every man’s wardrobe (or least a pair of dress shoes). 

My favorite dress boots are the Beckett Simonon Elliot. They’re very similar to Oxfords, which are among the most formal, so you’re getting all the class and sophistication and sprinkling a little extra manliness on top. 

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Beckett Simonon Elliot Balmoral Boot
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There are plenty of other excellent dress boot options, too. So even if you’re trudging around in the winter, don’t think you can’t have a stylish, classy boot that can also perform in tough elements—those exist, too. 

The best thing about a fantastic pair of boots is this: you can dress simply with the rest of your outfit and let your boots do the talking. 

FAQs

Are dress boots in style?

Dress boots are certainly in style. And the best part about buying a high quality pair of dress boots is that they’ll never go out of style. Dress boots are a staple in a sophisticated man’s wardrobe.

How should men dress with dress boots?

You can pair your dress boots with jeans and t-shirt to mix formalities and get a casual and hip look. Or you can go fully classy with a suit. If you have a great pair of boots, you can let them be the star of the show and dress very simply. Dress boots don’t always need to be worn in a formal situation, and can lend class to any outfit.

What are considered dress boots?

To be considered a dress boot, the boot must be made with fine leather, typically full grain, and usually has the upper shape of an Oxford shoe. However, Chelsea boots are becoming more formal with changing style standards, so they too can qualify as a dress boot, so long as the sole is relatively low-profile and the leather is clean, dark, and mark-free.

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