When I was a kid, my father used to tell me, “every man needs at least 3 pairs of good quality dress shoes.” I took his advice to heart. Of course it was a different time back then.
These days you would be lucky to find a man who owns even one pair of dress shoes. But you know what they say: the more things change, the more they stay the same. My father’s advice is true today as it was all those years ago. Some things never go out of style. Dress shoes are one of them.
Many men do not pay attention to dress shoes because they do not understand the importance of dress shoes. And even if they do, they are clueless about dress shoes. There are so many types of dress shoes out there. Which one to wear for which occasion? It is overwhelming.
In this article, we will go over the importance of having good quality dress shoes as part of your wardrobe. Then we will look at the various types of dress shoes in detail. By the end of this article you will be knowledgeable enough to make informed choices about dress shoes.
Table of Contents
Why Should Dress Shoes be a Part of Every Man’s Wardrobe
You are on a first date.
She walks in. Looking beautiful in a lovely dress. Will this be love at first sight?
She sees you in the crowd, and her eyes light up. She notices the impeccable jacket you are wearing.
She walks up to you and breaks into the brightest smile. She lightly bites her lips and lowers her head until her eyes rest upon your…
dirty, tattered sneakers.
In an instant, her smile is extinguished.
Don’t make that mistake. Your shoes do matter. They say a lot about who you are and how you see yourself.
Still need more convincing? Consider these reasons:
- Dress shoes complete your outfit: You could be wearing the best handcrafted jacket and pants, but without a nice pair of dress shoes to complement your other clothing items, your outfit is incomplete. An outfit without a pair of dress shoes is akin to a building without a capstone. It is missing its soul.
- Dress shoes communicate your status quietly: Yes, a $400,000 Patek Philippe tourbillon minute repeater on your wrist is a great way to convey status, but it is also a bit of a case of trying too hard. Not to mention not everyone has $400,000 burning a hole in his pocket. A quality pair of dress shoes, on the other hand, reveal your status in an understated manner. It also costs a lot less than a Patek Philippe.
- Dress shoes signal your attention to details: Yes, that bespoke single needle shirt you are wearing shows great attention to detail. So does your suit jacket with functioning sleeve buttons. But nothing beats a pair of dress shoes that are properly maintained and polished. And, it’s worth repeating, dress shoes do it quietly.
- Women notice dress shoes: When it comes to first impression, shoes are one of the first things a woman notices about a man. In survey after survey, women admit to having a weakness for men in a nice pair of dress shoes. Dress shoes represent an opportunity to impress a woman. Don’t let that slip.
Tip: Think of your shoes as investments. Dress shoes are the blue chips.
Types of Dress Shoes For Men
Now that you recognize the importance of dress shoes, it is time to understand the various types of dress shoes. All dress shoes aren’t equal. Each style of dress shoes serves its own niche. Appreciate these styles, and their niches and yourself won’t make sartorial faux pas.
The Oxford (aka Balmoral)
Oxfords are without a doubt the most timeless and classic dress shoes. Every man needs at least one pair of Oxfords in his closet. Oxfords are quite formal, but they are also an excellent choice for everyday wear.
What Does It Look Like: The most recognizable feature of an Oxford shoe is its “closed lacing,” in which the inside and outside quarters are stitched underneath the vamp (the upper front part of a shoe.) Originally, Oxfords were formal and plain shoes made of leather.
They have since evolved into a range of styles that cover both formal and less formal occasions. Nowadays, Oxfords can be plain or patterned, and they can be made from a variety of materials, including leather, faux leather, suede, and canvas.
A Short History: Oxfords were created in Scotland and Ireland, where they are sometimes called Balmorals after the Balmoral castle. In the early 1800s, they became popular among college students, especially those at Oxford University, seeking to rebel against the then ubiquitous half-boot style Oxonian shoes. After that, they became known as Oxfords.
How to Wear: From its formal root the Oxford has grown into a versatile shoe suitable for a whole host of occasions.
- Stick to the classic color combinations such as charcoal suit with black Oxfords or navy suit with dark brown Oxfords.
- Same idea with your socks: classic colors like black, navy, and gray are your best bets.
- Pick from a broader range of colors from black to brown to oxblood to blue.
- Experiment with different materials including leather, suede, or canvas.
- Pair them up with slim cut raw denim jeans or straight leg gray moleskin chinos.
- Wear them with colorful socks for extra dash.
- Formal Wear:
- If you are going to wear Oxfords with a tuxedo, stick with black patent leather.
The Derby (aka Blucher)
Derbies are similar to Oxfords but somewhat less formal, which makes them more versatile. They can be worn on all sorts of occasions, from formal business to everyday casual wear. In America, Derbies are also known as Bluchers.
What Does It Look Like: Many people mistake Derbies for Oxfords as they look similar, and the differences are subtle at best. As opposed to Oxfords’ “closed lacing,” Derbies feature an “opening lacing” system.
For Oxfords, the inside and outside quarters are stitched underneath the vamp. For Derbies, the quarters are stitched on top of the vamp. This “open lacing” leads to a roomier, more comfortable fit, which is particularly suitable for people with a high arch or a high instep.
A Short History: According to the legend, the Derby was created in the early 19th century for Edward Smith-Stanley, the 14th Earl of Derby. The Earl purportedly had very large feet and high arches, which made it very uncomfortable for him to wear regular boots or Oxford shoes.
Consequently, his shoemaker developed an “open lacing” system to better accommodate his oversized feet. By the 1850s, Derby’s roomier fit had made it a popular choice for sporting and hunting. By the turn of the 20th century, Derby was no longer limited to sporting and had become acceptable for wear in town.
How to Wear: Derbies are more casual than Oxfords. That also makes them more versatile.
- Given Derby’s sporting root you might not want to wear Derbies with a formal suit.
- But Derby is a great choice for business settings other than the most formal environments.
- The colors black, brown, and oxblood are your best bets.
- Feel free to experiment with colors – black, brown, oxblood, blue, etc.
- Go with suede or canvas for a more casual look.
- Pair them up with dress pants or chinos.
- For jeans, go with skinny black jeans for a sleek look or whiskered distressed jeans for a more contrasted look.
Men’s Monk Shoes
Monk shoe has been gaining popularity rapidly in recent years. It sits somewhere between Oxford and Derby on the formalness spectrum: less formal than Oxford but more formal than Derby.
What Does It Look Like: Monk shoe has no lacing. Instead, it is fastened by straps and buckles. There can be one, two, or even three straps per shoe. This unique strap and buckle system gives monk shoe a unique look with a certain edge and dash that other styles lack.
A Short History: The exact origin of monk strap shoes has already been lost to history. Legend has it that a medieval monk at a monastery in the Alps in the 15th century created the first monk strap shoes when he tried to making something that offered more protection than the usual open toe monk sandals.
A pilgrim to the monastery visiting from England saw this new style of shoes and became so enamored that he brought a pair back home with him. This new monk shoes caught on quickly in England, and from there, it spread to the rest of the Western world like wildfire.
How to Wear: Monk shoes are very versatile. Their unique strap design can turn your shoes into the focal point of attention for your entire outfit. Take advantage of that to stand out from the crowd.
- Monk shoes work in even formal business settings. They are like an edgier cousin of Oxfords’. Stick to black or brown monks and wear them with formal suits.
- They also look good with less formal outfits and cuffed dress pants.
- Monk strap tends to draw attention to itself so make sure this is what you want to achieve.
- Monk shoes possess a certain old-world mystique. Play up to that mystique by pairing monks with a pair of checkered cigarette pants or overdyed black skinny jeans.
- Try suede or canvas for a more varied look.
- For the truly adventurous, two-tone monk shoes may just be what you are looking for.
- Pair them up with distressed bootcut jeans for a hint of irony.
Mens’ s Chelsea Boot
Chelsea boots are forever linked to the Swinging Sixties and the mod scene. They are just oozing with sleek sophistication. They are also one of the easiest ways you will ever find to quickly amp up your style quotient.
What Does It Look Like: Chelsea boot is an ankle boot with an elastic side gusset. It often has a loop of fabric on the back, enabling the boot to be pulled on. This elastic gusset and loop system enables a Chelsea boot to be put on and slip off easily. The lack of laces makes for a modern and minimalist silhouette.
A Short History:
- Chelsea boot was created by Queen Victoria’s shoemaker J. Sparks-Hall in the 19th century as a riding boot for the upper crust of British society. It quickly became a favorite among horse riders. Queen Victoria was said to be a fan herself.
- During the 1960s, Chelsea boot caught the public’s imagination and became a cultural icon. It came to symbolize the aesthetics of the Swinging London. These boots were worn by everyone from the Beatles to the Rolling Stones to Pink Floyd.
How to Wear: Chelsea boot can add edge to a business suit and class to a casual outfit. It is magical.
- For the most conservative businesses, Chelsea boot is not a good choice.
- For the more creative or innovative settings, Chelsea boot is a quick way to dash up a suit.
- Pay homage to the mod heritage of Chelsea boots, wear them with slim pinstripe pants, and a mohair v-neck sweater.
- Try pairing black Chelsea boots with black skinny jeans. You’d be ready to join a band.
- For suede Chelsea boots, a pair of cuffed raw indigo jeans would complete the look perfectly.
Men’s Dress Boots
Dress boot is like a boot version of Oxford. It is less formal than Oxford and more versatile.
What Does It Look Like: Like Oxford, dress boot features “close lacing.” It looks like an Oxford but with a longer shaft that covers the wearer’s ankle.
A Short History: Dress boot emerged in the Victorian era as footwear for formal occasions. As time went by, its role as formal footwear declined and instead became a popular footwear for inclement weather.
How to Wear: Dress boot can be dressed up or dressed down depending on your outfit.
- Avoid dress boots for the most conservative businesses like banking or corporate law.
- For more casual business settings, dress boots in black or brown go well with suits.
- Dress boots should be sleek and refined, not clunky.
- Pair black minimalist dress boots with herringbone pants for a nice contrast.
- Wear brown dress boots with raw indigo bootcut jeans with cuffs.
- Avoid suede dress boots.
Men’s Chukka Boot
Chukkas are ankle boots that can be either formal or casual. They are truly versatile.
What Does It Look Like: Chukkas are ankle boots with “open lacing” and 2 or 3 pairs of eyelets. They are made from either leather or suede and come with leather or rubber soles.
A Short History: Chukka boot traces its root back to the desert boots worn by the British soldiers in the North African Campaign of World War II.
How to Wear: While Chukka boots were born as rugged footwear in the military, they have since evolved into a versatile style that can be either formal or casual.
- Chukka boots are not appropriate for the most formal environments
- For business casual settings, go with black leather Chukka boots with thin leather soles
- For a rugged look, go with brown suede Chukka boots with thick rubber soles. Pair them with medium wash distressed bootcut jeans.
- Roll up jean legs for extra roughness
Formal Pump (Opera Pump)
Opera pumps are the most formal shoes.
- What Does It Look Like: Opera pump is a slip-on made of patent leather. It is typically decorated with a grosgrain bow.
- A Short History: Opera pump dates back to the early 18th century when European aristocrats wore laceless slip-ons in court and formal settings. It has changed little since then. It is the oldest men’s shoe style still in use.
- How to Wear: Typically, opera pumps are only worn with tuxedos at a white tie or black tie events.
An extremely versatile laceless slip-on shoe inspired by moccasin.
What Does It Look Like: Loafer has no lace. Some are decorated with a tassel or a metal ornament, others are minimalist. There is typically a seam that runs along the toe.
A Short History
- Loafer was created in the 19th century in London by the bespoke shoe company Wildsmith Shoes. The first loafer (“Wildsmith Loafer”) was a house slipper made for King George VI.
- In the 1930s, a shoe company in Maine invented the penny loafer, which quickly became an icon of preppy and Ivy League aesthetics.
How to Wear:
- Wear black or brown leather loafers with a navy suit to go full preppy.
- For business casual settings, pair brown loafers with tan khakis.
- Try matching suede loafers with distressed straight cut rolled jeans.
- Throw on a white cable knit sweater, and you’d look like you’ve just stepped out of a Ralph Lauren ad.
The Stylistic Details
There is more to men’s dress shoes than just the 8 types we covered above. Each type of dress shoe can also come with various stylistic details. The 4 main stylistic details found in men’s dress shoes are: wholecut, plain toe, cap toe, brogue.
In the following sections, we are going to look into these stylistic details one by one. In addition, we will see how different stylistic details can work with different types of dress shoes.
For the past few years, wholecut shoes have been getting more and more popular. As its name implies, a wholecut shoe is a shoe with an upper that is made from a single, flawless piece of leather. So how is that different from other styles?
Typically, dress shoe uppers are made from sewing together multiple pieces of leather. You can easily see stitches on a typical Oxford shoe or dress boot – those stitches show you the places where two pieces of leather are sewn together.
A wholecut shoe upper is made from one single piece of leather, which eliminates the presence of most stitches on the upper. This gives wholecut shoes a very clean and minimalist look. This sleek, clean look is what sets wholecut shoes apart.
Some people use the term “wholecut” to refer to Oxfords exclusively. But the stylistic detail of wholecut is not limited to Oxfords. More and more often, we are seeing the wholecut style appearing in other types of dress shoes. For example, there are wholecut monk shoes, whole cut dress boots, whole cut Chelsea boots, and so on.
Seamed vs. Seamless Wholecut
In terms of construction technique, there are two types of wholecut shoe: seamed and seamless.
- Seamed wholecut
This is the most common type of wholecut shoe. It is characterized by a vertical seam that runs down the heel counter at the back of the shoe. That seam is where the leather upper closes in on itself. This type of wholecut shoes can be made either by hand or by machine. Seamed wholecuts tend to be less expensive than seamless wholecuts.
- Seamless wholecut
Seamless wholecut gets rid of even that single seam on the heel. The entire upper is perfectly smooth and seamless. This type of wholecut shoe can only be made by hand and it requires a very high level of craftsmanship. As a result, seamless wholecuts are more expensive. Typically, you can only find them offered by high end shoemakers. Many are offered as made to measure or bespoke products.
Wholecut Shoes Leather Requirement
In general, wholecut shoes are more expensive than their non-wholecut counterparts for 3 reasons:
- Without the ability to stitch together multiple pieces of leather, a wholecut shoe requires a single larger piece of leather, which is more expensive than several smaller pieces of leather.
- When you are making a shoe out of several small pieces of leather, you can cut around imperfections and blemishes. You can’t do that with a wholecut shoe. For a wholecut shoe, you need a high quality, large piece of leather that is free of blemishes and has a consistent texture. This further increases the cost.
- From a technical point of view, wholecut shoes are among the most challenging to make. They require a high degree of craftsmanship. The manufacturing process is also more time consuming. Seamless wholecut shoes are even more challenging and can only be made by hand.
If you appreciate good craftsmanship and you are a connoisseur of the art of shoemaking, wholecut shoes are a great choice for you.
And if you are a fan of bespoke tailoring, you should consider seamless wholecuts. Pairing a bespoke suit with a pair of bespoke seamless wholecut Oxfords is quite simply the epitome of sartorial sophistication.
How to Wear Wholecut Shoes
Wholecut shoes are simple. They are minimalist. There are no stitches to interrupt the surface flow of the shoe uppers. This simplicity and minimalism give wholecut shoes an air of understated elegance.
They are not loud, not ornate. They do not call attention to themselves. This quality makes wholecut shoes a perfect way to “dress up” an outfit. They can be worn with a formal business suit or a smart casual jeans and sweater outfit. Here are some pairing ideas for you:
- Black patent seamless wholecut Oxfords with a tuxedo
- Burgundy wholecut monk shoes with a navy suit
- Chocolate wholecut Derbies with olive wool dress pants
- Black wholecut Chelsea boots with black moleskin pants
- Brown or beige suede wholecut Chukka boots with raw indigo straight leg jeans
While a pair of wholecut shoes can “dress up” an outfit, wholecut shoes themselves are also more formal than their non-wholecut counterparts. For example, wholecut Oxfords are more formal than regular Oxfords. Wholecut monk shoes are more formal than regular monk shoes.
Keep this in mind when you are picking your shoes for the occasion. You do not want to be overdressed. For instance, if an occasion calls for casual dress, a pair of wholecut Oxfords may be too formal. Instead, consider a pair of brogue Oxfords (more on that later.)
On the other hand, a pair of wholecut patent black Oxfords are good enough for all but the most formal white tie events that require formal pumps. Here are some examples:
Example of Seamless wholecut Oxford: Saint Crispin’s Seamless Oxford
Example of Wholecut Oxford: Paul Evans Men’s Martin Wholecut Oxford
Example of Wholecut Derby: Altan Bottier Wholecut Derby
Example of Seamless wholecut monk shoe: Signifer Wholecut Double Monk Shoe
Example of Wholecut Chelsea: Meermin Wholecut Chelsea Boot
Example of Wholecut loafer: Carmina Shoemaker Wholecut Loafer in Polo Suede
Plain-toe means there is no embellishment on the toe area of the shoe, resulting in a smooth and uninterrupted front area. Similar to wholecuts, plain-toe shoes have a clean and sleek look that gives out an air of elegance. While plain-toe shoes are not as formal as wholecuts, they are more formal than other styles such as cap-toes or brogues.
Just like wholecut, plain-toe is a stylistic element that can be found in different types of dress shoes. For example, there are plain-toe Oxfords, plain-toe Derbies, plain-toe Chukka boots, and so on.
Plain-toe Oxfords are appropriate for formal business settings such as banking or corporate law. In most cases, they are also formal enough for tuxedos.
For business casual, a pair of plain-toe Oxford may be a bit too much. For these occasions, you might want to choose something a tad less formal such as cap-toe Oxfords, Derbies, or monk shoes. Here are some example:
Example of Plain-toe Oxford: Allen Edmonds Carlyle Plain-Toe Oxford
Example of Plain-toe Derby: Ted Baker London Men’s Derby Lace-Up
Example of Plain-toe monk shoe: La Milano Men’s Plain Toe Single Monk Strap
Example of Plain-toe Chelsea boot: Clarks Men’s Paulson Up Chelsea Boot
Example of Plain-toe Chukka boot: Nunn Bush Men’s Lancaster Plain Toe Chukka Boot
In cap-toe shoes, an additional piece of leather, known as the toe cap, is stitched on top of the toe box.
Cap-toe shoes are less formal than plain-toe shoes. That can also make them a bit more versatile. For example, while plain-toe Oxfords would be too formal to be worn with jeans, cap-toe Oxfords do not have that problem.
Cap-toe can be found in many different types of shoes. You can have cap-toe Oxfords, cap-toe Derbies, cap-toe monk shoes, etc.
Some ideas on pairing cap-toes with clothing:
- Black cap-toe Oxfords with unwashed indigo jeans
- Burgundy cap-toe Chelsea boots with skinny tweed pants
- Brown cap-toe monk shoes with whiskered bootcut jeans
- Tan cap-toe Chukka boots with gray khakis
One thing to keep in mind, you should not wear cap-toe Oxfords with tuxedos. It is not appropriate. Here are some examples:
Example of Cap-toe Oxford: Anthony Veer Men’s Clinton Cap-Toe Oxford
Example of Cap-toe Derby: ECCO Men’s Biarritz Cap Toe
Example of Cap-toe monk shoe: La Milano Men’s Cap Toe Double Monk Strap
Example of Cap-toe Chelsea boot: Deer Stags Men’s Argos Chelsea Boot
Example of Cap-toe Chukka boot: STACY ADAMS Men’s Ashby Cap-Toe Lace-up Chukka Boot
Brogues traced their roots to a type of outdoor shoe in Scotland and Ireland made from untanned hides. These shoes were made to be worn by farmers to wade through waterlogged terrain such as a bog. To that end, they had perforations on their uppers to drain out water after the wearers stepped out of water. In s sense, they were the original water shoes!
The English word “brogue” comes from the Gaelic word “bròg” which means “shoe.”
Nowadays, no one wears brogues for treading through marshes anymore and the perforations have evolved to be purely decorative.
Some people consider brogue a separate type of shoe that is mutually exclusive to other types such as Oxford and monk shoe. That is not quite correct. Brogue is defined by the decorative details found on the shoe upper. You can have the brogue details on all types of shoes: brogue Oxfords, brogue Derbies, brogue monk shoes, brogue Chukka boots, etc.
Different Styles of Brogue
Brogue can be found on cap-toes, plain-toes, or even wholecuts. While there can be countless variations of brogues, traditionally 6 main styles of brogue are commonly seen: full brogue, blind brogue, austerity brogue, half brogue, quarter brogue, and longwing brogue.
- Full brogue
Full brogue has a pointed toe cap with 2 extensions (“wings”) that run along the sides of the shoe. This pointed toe cap with wings is called the “wingtip.” There are perforations on the wingtip.
Full brogue makes a shoe more casual. For example, a full brogue Oxford is more casual than a plain-toe or cap-toe Oxford.
Example of full brogue: Nunn Bush Men’s Nelson Wing Tip Oxford
- Blind brogue
A blind brogue is a full brogue without the toe cap. In other words, it is a plain-toe shoe with full brogue-like perforations that give the illusion of a wingtip toe cap.
Example of blind brogue: STACY ADAMS Men’s Alaire Wingtip Lace-up
- Austerity brogue
An austerity brogue is a full brogue without the perforations on the toe area. It is basically a shoe with a wingtip toe cap but no broguing, so technically it is not a brogue but is still called a brogue. Yeah, naming can be weird.
Example of austerity brogue: 3DM Lifestyle Austerity Brogue Oxford
- Half brogue (or semi-brogue)
Half brogue is like a full brogue, but instead of a pointed wingtip toe cap, it has a regular straight toe cap. There are perforations in the middle of and along the edge of the toe cap.
Half brogue is more formal than full brogue.
Example of half brogue: Unlisted by Kenneth Cole Men’s Cheer Lace Up B Oxford
- Quarter brogue
Quarter brogue is like a half brogue but without the decorative perforations in the middle of the toe cap. There are still perforations along the edge of the toe cap.
Quarter brogue is more formal than half brogue.
Example of quarter brogue: Stacy Adams Men’s Dickinson Cap-Toe Lace-up
- Longwing brogue
Longwing brogue is a full brogue with the “wings” of the wingtip toe cap extending all the way to the back of the shoe, meeting in the middle of the heel.
Example of longwing brogue: Bostonian Men’s No16 Soft Wing Oxford
As mentioned, brogue can be found in different types of shoes: brogue Oxfords, brogue monks, brogue Chelseas, etc.
Here are a few examples:
Example of Brogue Chelsea: Asher Green AG2632 Wingtip Chelsea Boots
Example of Brogue Monk: La Milano Men’s Suede Double Monk
Example of Brogue Chukka: Nunn Bush Men’s Odell Wingtip Chukka Boot
Example of Brogue Loafer: Nunn Bush Men’s Norris Wingtip Loafer
Example of Brogue Wholecut Oxford: Thomas Bird Ellington Wholecut Brogue Oxford
Putting It All Together
In this article, we have covered the 8 main types of dress shoes for men: Oxford, Derby, monk shoe, Chelsea boot, dress boot, Chukka boot, formal pump, and loafer. We have also looked at the 4 main stylistic details: wholecut, plain-toe, cap-toe, and brogue.
Even though these shoes are all considered dress shoes, they have varying degrees of formalness.
Without a doubt, a formal pump is the most formal shoe you can get for men, followed by an Oxford.
Both formal pump and Oxford are generally considered formal shoes.
The other 6 types of dress shoe – dress boot, monk shoe, Derby, Chelsea boot, Chukka boot, loafer – are considered semi-formal shoes.
A Word from Love At First Fit
In terms of stylistic details, wholecut is the most formal. A patent black wholecut Oxford with no broguing can double as an evening shoe. Plain-toe is less formal than wholecut but more formal than cap-toe.
Cap-toe Oxford is formal enough for the most conservative business settings but should not be worn with tuxedos. Brogue is the most informal, which means it is great for casual wear and for adding an extra edge to an outfit.
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