The 10 Best Dress Boots | Chelsea, Cap Toe, Best Value, and More

Dressing up with boots today can be a risqué endeavor. While people think all boots with suits make you look like Keanu Reeves, there are certain dress boots that can really elevate your look. (By the way, Keanu Reeves is a badass and can wear whatever he wants.) So to help you avoid any mistakes, tThese are our Top Ten picks for dress boots. They really have no order and they each present a different take on the dress boot. 

Table of Contents

What Is a Dress Boot?

The definition for dress boot is somewhat selective and prone to interpretation. (Like, well, all areas of fashion.) But to streamline the process, we’ll summarize the features into four simple criteria:


Usually dress boots are made of calfskin, which is extra smooth, or a leather that can make a good shine with the proper waxes and polishes. Suedes can sometimes work, but most meaty boot leathers, like kudu or pull up, usually aren’t dressy. 

brown thursday captain in sun
The Thursday Captain boot is known for its sleek silhouette


A really streamlined look. This means that a dress boot needs a thin outsole with no lugs, a very dynamic and sleek last and, of course, an elegant silhouette from the side and top view. A well-tailored outfit deserves an elegant shoe! Chunky boots have their place, but since your suit isn’t baggy then your boots shouldn’t be, either. (Your suit isn’t baggy, right?)

Leather or Thinner Rubber Outsole

Like most dress shoes, dress boots will usually have a single/double leather outsole or a rubber substitute like Dainite. The point is to really have a sleek look; no chonky Vibram lug soles or similarly outdoorsy looking soles. As you’ll see, slim rubber outsoles are usually more popular because dress boots are seen as a “tougher-but-just-as-elegant” alternative to dress shoes. 

whole cut carmina oxford
Carmina’s whole cut oxford is one single piece of leather: the top tier of simplicity.


The simpler, the better. This rule might be a bit less hard and fast, but people generally look for boots with less decoration: no broguing, fewer panels, even whole cut footwear. That’s why at the bespoke/really high-end level in shoe-making, you’ll see insane things like seamless wholecut oxfords. The same rule applies to boots!

thursday wingtip boot
The Wingtip boot from Thursday Boot Company

The Different Types of Dress Boots

Dress boots can range from a large variety. As you’ll see later on in the list, there’s things from wingtip derby boots all the way to really slim chelseas. In general, the most common are:

  • Cap-toe boot: one of the most common style of all boots with a panel over the toe. Cap toes were originally for better durability, but on a dress boot it’s decorative. Cap-toes are great for making a stunning polish stand out!
  • Plain-toe boot: similar to the cap-toe, just without that leather panel on the toe. The plain-toe can be seen as more formal, as it’s simpler than the cap-toe equivalent. 
  • Quarter/Half/Full brogue boot: variations of brogue boots, from the quarter brogue only having broguing along the cap toe, while the full brogue will have full decorations, toe medallions and all! (See Trickers’ example above.)
  • Wingtip boots: these are similar to full brogues (and are sometimes referred to as full brogues) with the exception of a wingtip-shape on the cap toe. These can be on the more casual side of the dress boot spectrum, but something like traditional English country wear can make these look dandy!
  • Chelsea boots: a really trendy boot with no lacing, but instead is secured with elastic goring on either side of the boot’s shaft. The chelsea boot can be an extremely versatile piece, and can be dressed up or down depending on the last and the leather — just like lace ups! An ideal dress Chelsea is the one from Carmina.
  • Balmoral boots: think of this one as an oxford shoe extended to go over your ankles. This is the ultimate choice for the gentleman that enjoys formalwear but wants tougher footwear than the average. 

Of course, the field is far larger than these few. There’s a huge amount of variations and rare styles that are not accounted for!

alden cap toe plaza boot 3914
Image via The Shoe Mart

1. Best Made American Dress Boot: Alden Cap Toe Plaza Boot (3914) ($595)

The Alden brand is reminiscent of absolute quality. Alden of New England was founded in 1884 by Charles H. Alden. Their factory was founded in Middleborough, Massachusetts where they still reside today. In the past, the company’s focus was primarily orthopedic, in addition to their high-quality main line made in small batches via select high end retailers.

Alden today is similar but different; they serve the niche market of small batch production, boutique experience, only having a few self-owned retail stores but many high-end retailers such as J Crew, Ealdwine Raleigh or The Shoe Mart. Their current line mainly consists of dress shoes, loafers and handsome boots such as the famous Indy boot. Alden is especially famous for their extensive use of Horween’s Shell Cordovan, available in many models, including many dress boot varieties.

Alden Cap Toe Plaza Boot Highlights

This style is known as the cap-toe boot, sometimes the Plaza boot. Generally, this style is somewhat casual, but it can be dressed up, like in the case of these Aldens! With a lovely burnished calfskin, double leather soles and no speed hooks, this boot makes for a tough, no nonsense dress boot. If there was one boot that you had to wear for the rest of your life, these are probably a strong candidate. On top of that, Alden’s lasts are known for their extreme comfort and the Plaza last that these are built on is no exception!

black alden cap toe
The shoe is also available in brown (3912) or this black (3917) at The Shoe Mart

Who Should Buy the Alden 3914 Cap Toe Plaza Boot

  • The style is absolutely versatile. There’s so many ways to combine this boot with jeans, chinos and with the right slacks, it looks killer. 
  • In combination with their last, double leather soles and triple ribbed shank, these boots make for a really comfortable fit. All this is especially important if you stand all day; you’ll need that support.
  • Alden has a ton of sizes and widths available; they can range up to 6-13 in length and B-EEE in width. Chances are you can find the right size for the perfect fit. Plus, there’s many forums out there that can help you decide on your size if needed!
  • If you’re a big proponent of made in USA, these Aldens are 

Who Shouldn’t Buy the Alden 3914 Cap Toe Boot

  • Although their last are comfortable, some say the profile of them is rather chunky. You don’t need to look further when comparing them to say, a pair of Carminas. Some people may dislike the more clunky American look, I personally believe it’s charming!
  • At close to $600 on Shoe Mart, these boots can get pricey. At this point really, you’re paying for the made in USA workmanship. 

The Alden Cap Toe Boot can make a great dressy option for those who may not want a full on dress boot and need the comfort and support. 

[Get your own Alden 3914 Boots here!]

thursday cavalier chelsea boot new york

2. Best Value Dress Chelsea Boot: Thursday Boot Company’s Cavalier ($199)

You can’t go around the internet looking at boots without knowing about Thursday Boot Company. In addition to being marketing masters, the mission of TBC is to provide “ridiculously high quality footwear at honest prices”. They were started by two friends getting tired of wanting a boot that isn’t bulky like a work boot, but not overpriced and delicate like the designer stuff. They went ahead and made a great boot, put it up on Kickstarter, and the rest is history!

Thursday Boot Company’s Cavalier Highlights

The model in question is the Cavalier. This is their dressy variant of a chelsea boot, as their other chelsea models, like the Duke, are more akin to a rugged look. (You can actually see a comparison of the Cavalier versus the Duke here.)

The chelsea style in many ways was really meant as a dressy alternative. It follows the rule of simplicity = elegance and in the case of the Cavalier, the boot is rather elegant. Being built on their dress shoe last, the Cavalier presents a really sleek silhouette and fantastically smooth, rich leathers. We also can’t forget Finally, the outsole is a really interesting take on a leather sole. They take the leather and put these Dainite-like dimples to increase grip and wear resistance.

Who Should Buy Thursday’s Cavalier

  • TBC’s bang for buck is off the charts; a resoleable Goodyear welted, full-grain upper and great-looking chelsea for under $200 is hard to beat. 
  • TBC approaches comfort from the modern perspective; think of a sneaker, nice, plush and lightweight. TBC makes their boots that way with poron insoles, cork filler and leather  midsoles. This can make for a really comfortable experience for the right person!
  • The Chelsea boot style although a trend now, is something that has been here for a while and is here to stay. It’s classic, sleek and can be easily dressed up or down.
  • Finally, the Chelsea allows for an easier boot to put on, as laces can be cumbersome at times. 

Who Shouldn’t Buy Thursday’s Cavalier

  • The Cavalier is not built in a heritage manner; there’s no veg tan insole that will mold to your foot, and that may worry some about the boot’s longevity. 

Thursday’s Cavalier is a great pick for those starting out in the boot world and need something quality but affordable. I have a pair of TBC’s and I highly recommend them, whether a starter or looking for something new.

[Shop the Thursday Boot Company Cavalier here!]

crockett jones kew chukka
Image via Crockett & Jones

3. Best Dress Chukka Boot: Crockett & Jones Kew Chukka ($840)

There are few shoemakers in the world like Crockett & Jones, who sit alongside some of the highest end footwear manufacturers on Earth. Their origins start in 1879 in Northampton, England when Mr. Jones and Sir Crockett began the company focusing on mens boots. Their quintessentially English heritage shows today, and their offerings are now made with durability and classic taste.

Crockett & Jones Kew Chukka Highlights

Although derived from military and sporting backgrounds (according to their website), the Kew Chukka in this format is absolutely stunning in combination with the business ensemble. The upper is made of a gorgeous willow grain leather, constructed on their Goodyear welt with a thick leather insole and a proprietary Dainite-style outsole. In terms of English bootmaking, you really can’t get more classic than this. When buying C&J, you’re getting some of the best made production boots in the world. 

crockett jones kew
Image via Crockett & Jones on Facebook

Who Should Buy Crockett & Jones’ Kew Chukka

  • Men who think long term; boots like this aren’t the kind to last just a few resoles before they get tossed out. These chukkas are heirloom quality, as many C&J’s have gone through decades of wear and tear. It’s really more of an investment.
  • You can be rest assured that C&J is using the best materials and construction methods; with a rich history of over 120+ years of using Goodyear welts, European hides and more. There’s really no expense spared. 
  • Guys who want versatility; the rich brown color of the boot makes for an insanely versatile piece while the willow grain look makes the boot a lot more resilient in feel than the calfskin dress boots are usually made of. The result is a boot that can be easily tied up and dressed up, and it cleans up really well with a lovely blazer/trouser combination. 
  • Friggin’ James Bond wears C&Js!

Who Shouldn’t Buy Crockett & Jones’ Kew Chukka

  • The boot’s only hold back is a big one: the price is astronomically high! But people that buy a C&J understand that their boots go beyond face value: there are plenty of more refined things like last, stitches per inch and more. 

If the Crockett & Jones line suits Daniel Craig, it will suit you. The classic English look leaves for a very upscale feel that although is costly, makes for the best in footwear experiences. 

[Your Crockett & Jones Kew Chukkas are here, Mr. Bond]

allen edmonds dalton wingtips
Image via Allen Edmonds

4. Best Wingtip Dress Boot: Allen Edmonds Dalton ($725)

We’re not done with American footwear just yet! While Alden serves for the boot nerd in us, Allen Edmonds is where a lot of us start and frankly, is a company worth staying with. Allen Edmonds is an American footwear company started in 1922 as a dress shoe company. They’re very well-known for their dress shoe models like the Park Avenue or their rugged boots like the Higgins Mill. Their dress boots however, are somewhat of a hidden gem.

Allen Edmonds Dalton Highlights

You don’t see many wingtip dress boots, but the Dalton pulls off the rare style really well. It’s a rugged, handsome look. In our specific example, we’re looking at the coveted shell cordovan model, an expensive leather made from horse hindquarters. These boots are constructed using a hefty 360 degree Goodyear welt, making the boot really easy to resole for your cobbler. The coolest part, however is the hard leather insole; it may not seem comfortable at first, but thanks to the cork inlay and double leather outsoles, this insole will form to your feet for a custom-like feel. 

allen edmonds cordovan daltons
Image via Allen Edmonds

Who Should Buy Allen Edmonds Dalton Highlights

  • Although fairly pricey, AE typically has a good sale every few months, making even this shell cordovan model a bargain. 
  • Most Goodyear-welted AEs are made in the US of A, making it the proper choice for those wanting to keep their money within the US.
  • The 511 last they are built on is the same one as their longwing; it is roomy and comfortable. Nothing beats a double leather sole!
  • AE’s recrafting program is really great! Their services are well-priced and provide a great value with replacement of welt, sole, heels, a shine-up on the uppers and finally, new laces. 
  • The wingtip style is super dandy. Although a fairly rare style, you’ll be surprised how good it looks when paired just right.
  • The Horween Shell Model here is simply stunning. For lovers of shell cordovan, this is it. Of course, their calfskin version is beautiful as well.

Who Shouldn’t Buy Allen Edmonds Dalton

  • The brand has gone under big scrutiny for really lowering their bar on QC. There are plenty of forums showing shoes not properly lasted, badly stitched soles and more. All this means is that you should go over your boots with a fine toothed comb before wearing them outside and making them un-returnable.
  • Their last is indeed comfortable for many, but it’s not the most refined, sleek last on Earth. 

This boot is definitely a statement piece for your wardrobe. The Allen Edmonds Dalton is a beautiful boot that provides a beefy look and feel for those that need that.

[Allen Edmonds Dalton — or you can get them in cheaper leathers for under $500 here]

beckett simonon fonseca
Image via Beckett Simonon

5. Best Oxford-style Boot: Beckett Simonon Fonseca ($239)

Beckett Simonon is a little like Thursday Boot Company, started by two friends wanting to make a good product at an affordable price, completely cutting the middleman. They went a step further, though, by making the process a made-to-order, which saves on the cost of warehousing but also increases the wait time: you can expect to wait one to three months for a pair of these shoes.  Their focus is primarily on dressier shoes and boots like a balmoral boot or oxford. 

Beckett Simonon Fonseca Highlights

The oxford is the classic choice when dressing up. The Fonseca boot from Beckett Simonon offers a very elegant solution to guys who want a boot that’s formal, utilizing oxford style shoes in all means in a chukka-like package. Beckett Simonon focuses on dressier applications at great prices and their mastery of this shows in their Fonseca boot. 

The Fonseca boot utilizes a lot of quality materials in a stylish package. It uses gold-rated Italian leather, so you can be rest assured that the leather is properly sourced. Their packaging is also fantastic, providing you two very nice shoe bags and insoles. On the topic of looks, you really can’t get more elegant than this in a modern sense. These can definitely dress up with your suit — plus they come in five colors.

beckett simonon fonseca brown
Image via Beckett Simonon

Who Should Buy Beckett Simonon’s Fonseca

  • Fonseca really combines the best of both styles presented, the structure and ankle support of a chukka boot and the elegance & function of an oxford shoe. 
  • At a really affordable price, there’s really no competition for this boot. Especially once you combine our 20% off coupon — use STRIDE at checkout to nab it!
  • The materials and construction used are very nice for the price, utilizing Italian veg-tanned uppers, durable leather soles, and what they call a resoleable blake stitch. 

Who Shouldn’t Buy Beckett Simonon’s Fonseca

  • If you need these boots now, you really can’t do so. Their wait times on ordering these boots is about 8-10 weeks before they even ship out. Although this made-to-order format makes their products more affordable, it also makes them a long wait.
  • Despite being called a resoleable Blake stitch, not all cobblers will be able to resole these. Most will, though.

Beckett Simonon’s Fonseca makes for a very compelling package for the dandy, patient fellow. Despite the wait time, you can expect a great value out of these elegant boots.


carmina chelsea on feet sunlight

6. Best High End Chelsea Boot: Carmina Chelsea ($570)

Carmina is the premier brand in Europe, tracing their roots to the late 19th century to Matias Pujada, a fine shoemaker in Spain. Today, the Carmina brand is run from the descendants of Pujada, preserving their finely crafted feel. Although another brand known for their shoes, their boot catalog is large, akin to being a kid in a candy store. After the initial awe, you’ll find yourself really attracted to their Chelseas, something of a staple for Carmina in recent years.

Carmina Chelsea Highlights

The Chelsea boots shown here are on their Simpson last and also have a unique look compared to their other boots; it’s RM Williams-esque but in an even more elegant package. The last is really elegant and shapely. Carmina also utilizes some of the best leathers around, and they’re known for really fine calfskin known as box calf, seen above. Finally, and surprisingly to many, these boots are Goodyear-welted. Usually, something like this is crafted with a blake stitch, but because of their fine artistry, they can fit a welt fine enough to fit the sleek chelsea boot image while still being tough and easily resoleable. 

Who Should Buy Carmina Chelsea Boot

  • Carmina, in the sense of craftsmanship and value, are really hard to beat. Despite a high price tag, the boots deliver that value extraordinary well, giving competitors twice the cost a run for their money.
  • The Goodyear welt makes them very easy to resole, giving them great longevity.
  • Boots this sleek shouldn’t be this versatile and yet these are. Though a current trend to pair slim boots with edgy clothing, the classic slim dark jeans and elegant chelsea will always look great.

Who Shouldn’t  Buy Carmina Chelsea Boots

  • The price, even at a good value, is still over 500 dollars. Needless to say, they are something to save up for!

Their Chelsea on the Simpson last is a staple from Carmina. It’s a very elegant choice for the very elegant individual. 


meermin 114077 balmoral
Image via Meermin

7. Best Affordable Balmoral Boot: Meermin Expresso Boot ($245)

We really can’t talk anything great value boots without looking at the value monster of Meermin. Although the family that created Meermin are related to Carmina and Yanko (two very high profile Spanish shoemakers), these two serve similar product lines at different price ranges. The Meermin name came into fruition around 2001, primarily serving the Japanese market. Their products came stateside relatively recently and are known to produce their shoes in China. Despite some people’s groans, they actually train their factory to make shoes up to their standards; if you’ve ever handled a pair of Meermins, you’ll notice they are definitely better made than many shoes twice the price point. 

Meermin Expresso Boot Highlights

The Meermin Balmoral boot takes many cues from many high end dress boots. Despite the similarities, this boot really makes you wonder why you pay so much for Edward Greens, (which cost over $1,500). These boots have an all leather Goodyear-welted construction, with a leather insole and even leather heel blocks! In addition to that, their uppers have a unique pattern, having a series of speed hooks for functional lacing and the lower half being a handsome oxford; the whole boot is also wrapped in full-grain french calfskin. These boots don’t really sacrifice any quality in their production line.

meermin 114077 brown
Image via Meermin

Who Should Buy Meermin Expresso Boots

  • There’s no sacrifice to quality. Virtually all their boots offer fantastic materials and if you’re so inclined, they have shell-cordovan models, handwelted and norvegese constructions on limited products!
  • At $250, you’re getting a steal! There’s nothing else in the market that can match this with a quick shipping time.
  • The Balmoral boot style is remarkably versatile. You can dress up with darker versions of this boot, or really spruce up a casual outfit.
  • The unlined suede on the shaft of the boot will make for a very soft and comfortable fit.

Who Shouldn’t Buy Meermin Expresso Boots

  • Meermin has the bad reputation for being really iffy with their customer service. This can probably be boiled down to them being a smaller company, but be sure to buy the right product when you get your boots!
  • Despite being real high quality products, they can have a longer break in than most boots. Now, we’re not talking about Red Wing levels of break-in period, but it does get up there. Don’t be surprised if these cause a bruise or two in their first few wears. It’s the Meermin way. 

The Meermin boot is personally my favorite. It can make for a really comfortable, stylish dress boot once you get over that break-in period!


grenson shoe no 1
Image via Grenson

8. Best Vintage Style Dress Boot: Grenson Shoe No. 1 ($735)

The Grenson name is up there with brands like Trickers in having a very British feel. The brand was one of the first factories in the world to have Goodyear welting machinery (in 1874, to be exact), making them one of the pioneers of the construction. Of course like many brands this old, their factories served both World Wars to make boots for British troops in WW1 and for many Allied forces in WW2. Their history makes wearing their products something to be proud of. 

Grenson Shoe No. 1 Highlights

The pick for Grenson on this list is actually a throwback to a model produced in 1912. The boot was originally produced for dressier occasions and today, certainly looks elegant in a charming way. The boot features the kidskin upper, a very soft, pliable and high shine leather usually made from a young goat hide (although there are versions made of lamb and calf). This makes for a leather that’ll take a polish really well, even a mirror shine.

The construction is the coolest part of this boot however. Although it is just a traditional Goodyear welt, the attention to detail is what makes this boot fascinating. There are items like the brass nails on the heel, decorations on the outsole and the exaggerated fudging on the welt that makes this boot feel vintage in all the right ways. 

grenson shoe number 1
Image via Grenson

Who Should Buy Grenson’s Shoe No. 1

  • There is almost nothing in the market that captures the vintage dress boot aesthetic more than this. The Edwardian style is unique and very handsome. 
  • Kidskin uppers make for a very comfortable experience; it’s the same leather they use for high-end leather gloves!
  • This is the boot for you if you nerd out on the details. There’s so much to look at, you could spend an afternoon just looking at these boots like a work of art. 

Who Shouldn’t Buy Grenson’s Shoe No. 1

  • Yeesh, that price! At the listed price of $710, you might not find the price justifiable. People that buy this boot, however, aren’t stopped by the price. 
  • The style can seem a little costume-y if you aren’t a fan of vintage looks. It’s not for everyone.

Grenson’s Shoe No. 1 is the perfect storm of history and boot nerd. I know this because I’m one myself! 


yeossal jodhpur
Image via Yeossal

9. Most Customizable Dress Boot: Yeossal Somerset Jodhpur (~$830)

The Jodhpur style is the cooler cousin of the Chelsea; it has its roots in the Indian sport of polo, where riders needed a boot to easily slip on. The Yeossal interpretation of this true to nature, but in an upscale, fancy package. Needless to say, you’re not going to wear these while playing polo. The brand Yeossal itself is fairly new and has only come into the spotlight for many around last year. Their idea is to provide a near bespoke level of shoemaking for half of the price. 

Yeossal Somerset Jodhpur Highlights

Yeossal is a proudly Chinese brand. They make their shoes in a very artisan fashion, with beautiful marbling on the uppers and the labor-intensive process of handwelting. The way they style their outsoles is stunning as well; this is one of the few boots made today with a thin fiddleback waist. The gorgeous upper design isn’t not an exact clone of traditional jodhpurs, but it’s a fresh take that will really elevate any outfit. On top of all this, the customization process is really extensive, letting you choose the leather, a last that suits you, and even the buckles available!

yeossal jodhpur boot
Image via Yeossal

Who Should Buy Yeossal Somerset Jodhpur

  • If you care about attention to detail and customization, Yeossal as a whole may appeal to you. 
  • These Jodhpurs have about the same level of versatility as chelseas. I mentioned this earlier, but many outfits will really benefit from this gorgeous boot.
  •  The near-bespoke level of quality makes you feel really special. You truly feel like these were made for you, rather than made in masses. 
  • The price, although high, is a steal compared to competitors that are half the price. (Think Edward Green or John Lobb. Yes, I’m serious!)

Who Shouldn’t Buy Yeossal Somerset Jodhpur

  • Artisans and people that have dedicated their life to the craft do make this, but some feel iffy about Chinese made goods.
  • There is a fairly long wait time for them. The website states a 2-3 month wait after your order is confirmed. 
  • While great value, it’s still over $600.

Yeossal’s Somerset Jodhpur is an absolute beauty. I believe this boot shows that quality comes from any corner of the world, in addition to outstanding value. 



J Fitzpatrick Puyallup
via J Fitzpatrick Footwear

10. Best Button-Up Dress Boot: J Fitzpatrick Puyallup Button Boot ($495)

There comes a time when a man wants something else. Something unique. These buttons boots, although a rare sight in today’s men’s fashion, are really not new at all; they were a staple of Edwardian dress-up in the late 19th to early 20th century. The recent comeback of these is a due to a trend of bringing vintage clothes back again; and honestly, these will probably stay and grow as an awesome alternative to say, the balmoral boot. J Fitzpatrick is one of the first to bring this style back from the dead to the wider internet space. If that name sounds familiar, he actually runs a blog called “The Shoe Snob”, very famous for having mouth watering pictures of gorgeous shoes & boots.

J Fitzpatrick Puyallup Button Boot Highlights

These Button boots are awesome; the details put into play are different but in a fun manner. The tweed on the shaft makes a very vibrant contrast, the broguing is very apparent and the buttons have a horn appearance. The result is a package that in theory sounds about as crazy as a Taft boot, makes for a harmonious art piece. Justin Fitzpatrick knows a thing or two when it comes to great design. On top of this, the boots are constructed with a Goodyear welt and really great materials, making this already intriguing package a good value.

j fitzpatrick carkeek
The Carkeek II is another colorway that may appeal to you.

Who Should Buy J Fitzpatrick Puyallup

  • The look is unique and if you give it a try, can actually make for a surprisingly wearable boot. This is especially so if you get it a down-to-Earth color like the one pictured.
  • There are really few alternatives on the market that even have this boot available; if they did, they cost much more. It’s really in a class of its own.
  • J Fitzpatrick’s products are solid; made in Spain like Carmina for sub-Carmina prices makes them really attractive. 

Who Shouldn’t Buy J Fitzpatrick Puyallup

  • Despite the style making a comeback, perhaps the look simply isn’t for you. I know that some may find it costume-like. 
  • In darker or more extreme colors, you may find difficulty pairing this with outfits beyond dressy occasions. This may or may not be a condition you find disadvantageous. 

Although not a pick for all people, if you love the look, it is an absolute must have in your wardrobe. The J Fitzpatrick Puyallup is for those who are different in the best ways.


What Do You Wear with Dress Boots?

Boots are infinitely versatile alone, but when you give them a dressy flair the opportunities for most of us are endless. I mean this in that most of us aren’t going to be hiking or working hard jobs often, but instead maybe a stroll in the park or perhaps under an office desk. The dress boot still maintains some ruggedness while being able to pair up more so than the usual chromexcel service boot. Here’s some ways to pair them!

via @theshoeque on Instagram


The awesome part about dress boots is their purpose; they serve as a tougher choice for their daintier shoe cousins. Dress boots can be paired with a dressy ensemble AND if casual enough, can make a really smart casual look. Above is an example of a gentleman killing it with an awesome pair of black AE Daltons.

Taft Jack phone
A grey blazer and blue slacks makes for a great base for dress boots. (Worn here with Taft Jacks.)

Business Casual

I’ve mentioned that the business casual spectrum is really wide; it’s from (what’s really smart casual) the oxford button down and chinos all the way to a heavy wool blazer and double-pleated trousers. The dress boot regardless is still a really elegant choice for anyone.  

erik mannby
via @erikmannby on Instagram

Business Formal

Boots in this realm can be controversial for some. Many purists say that the boot does not have a spot in this realm, but I beg to differ, As we’ve learned from many contenders in this list, the boot can be made for the dandy man. In fact, the irony is that one model on this list, the button boot, can be even worn to white tie events if you so choose. The business formal example above is a lovely dark green suit paired with some burgundy balmorals.

White & Black Tie/ Morning Dress

This style is rarely seen nowadays outside of the fanciest of balls or weddings. It used to be more commonplace at the turn of the last century, but has dwindled down since to a very rare occasion. Someone I immediately think of is Sven Raphael Schnider in a morning dress style ensemble and button boots here.

Wrapping Up

The boot world is shown to provide a wardrobe piece for anyone, from the rugged engineer boot lover to the dandy button boot enthusiast. There’s no doubt that the world of dress boots is really vast (trust me, I haven’t even covered the surface of what’s out there!). In this list, we presented ten of the best unique options around and provided some insight on what a dress boot is, their history, how to wear them and what can make them comfortable. Thank you for reading it here on Stridewise!

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I'm a native South Texan attending TAMIU, a part of the Texas A&M system! Currently a freelance journalist trying to form a trail into more professional matters. I'm by no means a good writer, but sometimes these guys hire me so I guess I'm not half bad? I focus on menswear, but I'm just a little bit of a nerd of the history of everything.Check out my Etsy shop where I make leather goods! In addition to that, I have a Youtube channel where I talk about all things heritage menswear and budget. Yes, quality menswear can be affordable!

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