Understanding Men’s Dress Shoes

Understanding Men’s Dress Shoes


The world of men's dress shoes is as wide as it is interesting. There are countless choices. Sometimes it can feel a bit overwhelming. We are burdened with so many options that it can't feel difficult to pick the right shoe for the right outfit.


In this article we're going to go over the basics of men's dress shoes. The essential elements. Different styles, how you should where them, things to look out for. We'll touch a bit on the quality of shoes and why that matters too.


If you're looking to get a better understanding of the different types of leather used in shoes, check out out dedicated leather types post.



Dress Shoe Basics



What To Look For and How They Should Fit


Let's start at the beginning. When you're looking to buy some new shoes there are something you should always have in mind. Regardless of what style or what brand you're looking to purchase.


To understand shoes you have to understand a bit about how they’re made.


A well made leather dress shoe has many components. The most important are the leather upper, the midsole and the outsole. The upper is the leather top of the shoe that you see. The outsole, or outer sole, is what is touching the ground when you walk. The midsole is what’s in-between. The insole is on top of the midsole. The insole is what your foot touches.


When it is made, the leather upper of the shoe is stretched over a piece of wood. This piece of wood roughly is shaped like a foot. It is called a “last.” This last is important. The shape of the last will determine the final shape of the shoe. Some lasts are long and pointy. Some lasts are short and stout. Some are tall, some are wide. This will greatly influence how the shoe feels and how it looks.



Photo of a pair of wooden shoe lasts

A pair of lasts. A bit like a foot. These can come in many different shapes and will influence how the shoe looks and fits when complete. 


So when you ask: Do men's dress shoes run big or small? It really depends on the last that was used to make them. Most makers have proprietary lasts. It adds to their branding. Its a shape and silhouette (and fit) you can only get from them.


Stetting the upper over the last can take anywhere from a few minutes to a few months. Quicker cheaper builds do it fast, to no surprise. High quality makers will leave the upper stretched over the last for weeks or months. This ensures the uppers truly form to the last and can keep their shape. Good things are almost always made slowly.


A longer and more pointed last (sometimes referred to as aggressive) will feel more formal. It will elongate the foot. It lends itself better to the sharp and crisp lines of dress pants. A more rounded shaped last is the opposite. The “softer” shape and silhouette that it produces lends itself better to casual wear.


Alden 975 long wing in #8 shell cordovan with zonkey boot black cap toe oxford side by side comparison to show differences in lasts



On top of looks, fit is important. The shape of the last will determine how a shoe might fit. Many people talk about having to buy different styles of shoes in different sizes. This is often because the last is shaped differently and will fit differently as a result. Some people have to go up in width to accommodate a more aggressive last. Some people down if more casual. It all depends on your foot and how it relates to the shape of the shoe.


This shaped upper is then attached to the midsole and/or outsole. How it is attached varies greatly and is beyond the scope of this article. For now we’ll simply categorize shoes into two main categories: Fabricated/Cemented or Glued, and “re-soleable.”


In fabricated shoes, the bottom of the shoe is permanently glued onto the top. Brands will do this because it is faster and cheaper to make. This makes it next to impossible to take off the sole and attach a new one on. Some skilled cobblers can manager to perform this job since they’ve adapted to this popular and inferior modern construction. It usually damages the upper. This is almost always a sign of bad quality and inferior materials. Avoid this construction if you can.


In “re-soleable” shoes you can easily remove the upper from the bottom of the shoe. This allows for a cobbler to resole your shoes much more easily. Methods vary drastically. Good Year Welt, Blake, Blake-Rapid, Hand Welted, and Norwegian/Norvegese being some of the popular choices. There are countless more.


In all of these methods the upper leather is stitched to the midsole or outsole in some way. These stitches can be removed. Once removed a cobbler can remove the sole of your shoe and replace it with a new one. Once one, they will restitch them together and voila. Your shoes have new life.


The midsole can be made of many different materials. High quality midsoles will either be made out of leather or cork. Sometimes a combination of the two. Yes, the same cork that goes into a wine stopper. It is soft, flexible, and can mold to your foot. It will have a break in period and will yield great comfort after.


A thick leather midsole will share many of the same properties. Shoes made with a generous cork midsole are often considered some of the most comfortable. You’re walking on a cushy amount of cork. Alden and Crockett & Jones come to mind.


Outsoles can come in many different varieties as well. Leather is most traditional for a sole. Rubber is becoming increasingly common. Some makers use a combination of both. What outsole is used is often very dependent of the style of the shoe. If it is a formal shoe you are more likely to see a leather sole. A rugged boot? Likely rubber. If you sole is leather but you wanted some rubber on it, some people will apply a Topy to it


Crockett & Jones Pembroke loafer in walnut scotchgrain up close to show stacked leather heels on a men's dress shoe


Another important element is the heel. Most heels are about 1 inch / 2.5cm in height. They are often made out of stacked leather or rubber. Why do men’s shoes have a heel? Some people think it is to make you feel taller. While this will happen with any heeled shoe, another element is that a heel can be replaced. Unlike, say, sneakers, when you wear through the heel of your shoes you can have them replaced.


On a well made shoe the upper leather, if treated well, will outlast the rest of the shoe. Quality upper leathers can last decades. The soles and heels much less. This makes some intuitive sense since you’re not walking on the uppers of your shoes. Their job isn’t as labor intensive.


When you’ve worn out the soles and/or heels of your shoes a competent cobbler can replace them for you! They don’t even have to replace them with the same thing you had before. You can resole your leather soled shoes with a rubber sole. Or vice versa. Often the cobbler will also replace the midsole at the same time.


Below is a diagram that shows some of the common terminology in describing a shoe. Helpful in discussing certain elements of your shoe, these are good to know. The vamp, for example, is the no-go zone when it comes to mirror polish.



Close up of Zonkey boot black cap toe oxford in calfskin leather men's dress shoe to shoe terminology.




How Should A Dress Shoe Fit?


This is a simple question, yet not an easy one. Many people don’t know what to look for. Since dress shoes are structured it is a different approach than you might use for sneakers. Some reports suggest up to 80% of men are wearing the wrong shoe size. 80%. Let’s discuss what to look for so that you find yourself in the knowledgeable part of that group.


A quick note on sizing before we talk about fitting. Size is only a number. Every maker has a different idea of what a standard width means. How a size 9D, for example, should fit. Different lasts will all fit differently. 


Not every maker using the same methods of sizing either. North American shoes and shoes from the UK are sized differently. A 9 in North American is usually an 8 in UK. You subtract 1. In Europe a size 9 is a 42.  There is a chart below that displays the width and sizes most common. Since every maker is a little different these are not 100% set in stone. Some makers think a 13 North American is a 46. Some say 47. 


This is all to say the size of your shoe doesn't matter. If you wore an 8 from one maker you might need a 9 or a 7 from another. 


Regardless of the number inside, you should be looking for three things in a well fitting shoe:


1. Does the widest part of my foot line up with the widest part of the shoe? Is the width comfortable?


Sometimes you’ll hear things like “are men's dress shoes supposed to be long?” This is in relation to how much empty space there can be at the end of the shoe near your toes. Unlike most sneakers, your toes will rarely come to the end of the shoe. That is ok. As above, this will depend on the last used for your shoe. It will depend on the shape. Many more formal shoes are longer and “pointier.” Your toes will be farther from the end. Sometimes 1 inch / 2.5cm or more.


Dack's brown loafer shown to display sizing of foot next to it


What is most important is the width. The widest part of your foot should line up with the widest part of your shoe. The “ball joints” or “knuckles” of your foot (metatarsophalangeal joints) should sit comfortably in your shoe.


If you put on a shoe and you find that your foot is too far forward or backwards in the shoe it likely doesn’t fit. Many people will try and go up a size to get more width at the widest part of their shoe. This can sometimes work, however it often doesn’t. What you gain in width you also gain in length. This extra length could mean that your foot isn’t placed properly in the shoe.


If you find the a shoe too narrow the answer is usually to go up a width or change lasts. A standard men’s shoe is a D width in North America and E width in the UK. North American widths go up by moving to the letter E and then adding more E’s. Going up one letter usually means going up one width in UK and those don’t stop at E. Note this varies by brand so ensure this applies to the shoe you’re buying.


A North American example: A 9D width in US is standard. A 9E width would be the same shoe but wider. A 9EE would be even wider. A 9EEE would be wider still. Etc. Allen Edmonds is a company known for making shoes in many different width. The reverse is true for going more narrow, except things stop at A. See the chart below for reference.


A UK example: A 9E width in UK sizing is standard. A 9F is wide width. A 9G is wider. A 9H is wider still. The reverse is true for going more narrow, except things stop at A. See the chart below for reference.


Size comparison chart showing UK sizing vs North American shoe sizing vs European shoe sizing


Do shoes stretch? Yes and no.


A shoe will stretch a bit and relax across the width near your toes. This is in part due to the leather giving way to your foot a bit and becoming a hint bigger. It is also due to your foot compressed and wearing in the midsole. As we spoke above, the midsole is often cork or leather. As these get worn in they get compressed. This compression will increase the amount of volume available in a shoe. So your shoe feels a bit roomier. It will only stretch a small amount. If you put on shoes and they feel like a vice, they aren’t going to loosen up that much. You should expect a very minimal amount of stretching. If they are very tight get a different size or last. Life is too short for painful shoes.


Shoes will NOT stretch in length. If you feel your toes touching the end of the shoe you should abandon it immediately. The heel and toe have structured elements inside of them that prevent from from stretching. A shoe that is too short will almost never work for you. Find something else.


So if a shoe is too short go up a size. If the shoe is a good length but too tight at your toes go up a width.


Note that when you go up a width you will get more room for your toes. You will also get more room for your heel, whether you like it or not. This brings us to our second point.


2. Does my heel feel secure in the shoe? Or does it feel like it’s slipping out when I walk?


You want your heel to be snug and comfortable in your shoes. If your shoes are too tight in the heel then they will bite or pinch your feet all day long. This will lead to a lot of discomfort and possibly blisters. The heel won’t stretch so this is likely a permanent thing.


If you the heel of your shoe is too big, you will have the opposite problem. Much more common to see, this is called “heel slip.” This is when you find your heel slipping out of the shoe when you walk. This can range from a little bit (a few millimetres) or a lot (your foot coming all the way out).


A touch of heel slip can be ok. When a shoe is new it is the stiffest it will ever be. The midsole and outsole are fresh and unworn. They haven’t been flexed at all yet. This means they will be snapping back into their neutral flat position with as much force as possible. Think about stretching a brand new rubber band. So while you’re walking and bending the shoe, it is snapping back into place and wanting to go flat.


After you’ve worn your shoes a bit this effect lessens. Think of an older rubber band. So now the shoe is more compliant. It fights back less.


So if you have new shoes that have a very small amount of heel slip, it should lessen with time.


Up close of men's leather dress loafer to display how men's shoes should fit. Close up of the heel


If your shoes have tons of heel slip it is likely a poor fit. You should look at going down a length and/or going down a width. If you can’t do either because of your toes, then it is time to find a different last. Different lasts will have different shapes for heels. Find one that works for you. The Alden Barrie last, for example, is known to be accommodating width wise for your toes without having too much room in the heel. Many people report it being their most comfortable last. As always, this depends your foot.


3. Is the shoe comfortable?


Simply put, is it comfy? Do you see yourself walking a few kilometres in these? Are you happy to have them on?


If the widest part of your foot is lined up with the widest part of the shoe. If your heel is snug and secure without being tight. Then you likely have comfy shoes. That said, walk around a bit a get a feel for them. At the end of the day you will be unlikely to want to wear shoes that feel bad. Regardless of how good they look or how sweet a deal they were. Fit is one of the most important elements of footwear. Much the same with clothing.


We often get asked “which men’s dress shoes are the most comfortable?” The answer is usually the same: the one’s that fit you best.


Note that none of these qualities involve you pressing down on the toe box of the shoe to test. When you’re trying on shoes, pressing down on the toe box can be a fatal mistake. First, it only gives you bad information. If your toes aren’t touching the end of the shoe (which you should be able to feel from your toes) then the shoe is long enough. How far your toes are in relation to the end depends on style. If the shoe is too long or not will depend on the width and how your heel feels.


Importantly, pressing down on the toe can damage your shoes! The toe box of a shoe has a stiffener inserted into it to make sure it keeps its shape. This can be hardened leather or plastic depending on the brand. Once this toe box is depressed and deformed, there isn’t much you can do to fix it. If you press down hard on the toe of your shoe you can cause a permanent dent. Please don’t press down on the toe box of shoes. It provides you no useful information and can damage your shoe.


Now that you understand more about how a shoe should fit, let’s talk about what styles are available and when you might want to wear them.


Men’s Dress Shoe Styles


There are countless styles of men’s shoes. While we don’t have the same variety as women, we have enough to keep us busy. We’re going to cover some of the most popular and most wearable styles. This is not an exhaustive list. Consider it a primer.


After this you'll understand when someone say oxford dress shoe or brogue shoe (both often misued).


What dress shoes are in style? This isn’t the question we’re looking to answer. Styles can come and go. What we find most important is to understand why you’d want to wear certain styles of shoes with certain outfits. If you understand the “why” you can come up with more combinations and be more confident in your choices.


Let’s discuss some general basics before we dive into specific styles. This will give you a better understanding of the mindset behind different styles.


Oxford vs derby (or Balmoral vs. Blucher).


Think of this as main category that many shoes fall into. Most shoes are one or the other. It is a simple distinction that is easy to make. It’ll also make a difference to the styling of the shoe so it is worth noting.


“An Oxford [aka balmoral] shoe is characterized by shoelace eyelets tabs that are attached under the vamp,[1] a feature termed "closed lacing".[2] This contrasts with Derbys, or bluchers, which have shoelace eyelets attached to the top of the vamp”




Crockett jones Pembroke shown with zonkeyboot cap toe oxford to shoe difference between derby and oxford shoe



There are many styles that can be considered an oxford shoe.


An Oxford is generally considered the more formal option. It is more simple. Some of the action is hidden underneath the vamp. A Derby shoe is more casual. This same logic also applies to boots. Balmoral boots are fairly rare and are seen as a more appropriate dress boot. Even if dress boot can seem a bit of an oxymoron at times, it can be executed well.


A rule of thumb is that oxfords are better for wearing with suits. Derby’s are better for wearing with sport coats and/or jeans.


Some people prefer to wear one over the other because of fit. Do you how a derby is made, the top can open up a bit more. This can be more accommodating for people a high instep. The opposite is true of an Oxford. It can’t open as much so it has less wiggle room. Some people with a lower instep or narrow foot might prefer this style simple for fit concerns.


Formal vs Casual


All things equal, a shoe with less going on is going to be more formal than a shoe with more. And the darker the shoe the more formal. That is why oxfords are more formal. They’re more plain.


Plainer and darker means more formal.


Think of it kind of like a suit. A very simple plain black suit or tuxedo is very formal. No flashy element. No embellishment. Simple straight black. Suitable for black tie or a funeral. This is due to its simplicity.


Similarly shoes that are simple are more formal. So a black whole cut or Oxford (more on this shortly) is about as formal as it gets.


Often more formal shoes will be shaped more aggressively. More pointy. This is because more formal shoes are often worn with more formal clothing. Suits, sport jackets, tuxedoes. When wearing a crisp suit or dress pant you often have a lot of sharp lines. Suits have sharper lines on the lapels, the crease in the dress pant, and sometimes the shoulder. These sharper lines add structure. So too does a sharper line in your shoe. They compliment each other well. They’re visually and aesthetically consistent.


Plain + dark + pointy = formal.


The more you add to the left of the equation the more formal the outcome.


The opposite is also true.


As you start to add things to a shoe it becomes less formal. Think of things like brogues. These are the little “holes” that you find on shoes. So popular that some people simply call a shoe with brogues a pair of brogues. A wingtip is another example. Anything with a medallion or design of any kind. These can make a shoe interesting. They also make it more casual.


Alden 975 long wing in #8 shell cordovan with zonkey boot black cap toe oxford side by side comparison to show differences in lasts


Colour plays an important role. As a shoe gets lighter in colour it is generally more casual. A tan is more casual than a dark brown, all other things being equal. This should come as no surprise. A cornflower blue suit would be too casual for a funeral. A midnight navy would likely be appropriate.


Shape is the last metric. A rounder, more stout, softer shaped shoe is more casual. You will find this pairs well with the colours and the pattens I just mentioned. A soft shaped wingtip Blucher is a wonderful casual style. The silhouette works well for more casual clothing. Things like casual slacks or jeans. If you wear soft shouldered sport jackets and denim, a similarly “dressed down” shoe will compliment it nicely. This softer rounder shape gives off an air of ease. It’s not fussy. It’s a more comfortable shape to match a more comfortable look.


Less plain + lighter colours + softer shape = more casual.


These are guidelines, not rules. And yes, there are models of shoes that blur the lines between these two. There is overlap. There are exceptions. The rules are meant to guide us not bind us. Understanding them will help you decide when you break the rules and when to bend them.


Keep these in mind as we go through some popular styles. Pick what works best for you and your closet.


A few more pieces of terminology that are good to know.


Brogues: These are the tiny little “holes” that are places all over shoes. Note they aren’t actually holes since they don’t go all the way through the leather. (In most cases). They are more like faux holes. They add visual interest to a shoe and help make them a bit more casual. 

Crockett jones Pembroke shown with zonkeyboot cap toe oxford to show what are brogues. One brogue shoe and one shoe without brogues


It is NOT a shoe style, per se. People will often casually refer to a pair of shoes that has brogues as a “pair of brogues.” Any style can have brogues though. A cap toe Oxford. A derby boot. A wingtip Blucher. A shoe can have a lot of brogues or a small amount of brogues. Its up to the maker.


Medallion: This refers to a special brogue pattern that is often found on the toe cap of a shoe. They can come in many different styles. Most are somewhat similar and a bit different to tell apart. Some can be as intricate as a skull and cross bones. More often than not you’ll simply need to know whether or not the shoe has a medallion. Which type is usually less important.

  Crockett jones Pembroke shown with alden 975 long wing blucher in shell cordovan to show different medallion patterns


Apron: This is a series of stitches that circumnavigate the toe cap and part of the vamp of a shoe. Sometimes referred to as a “Moc-Toe” (which is one type of apron). This usually plays no structural role on the shoe. It is added to add some visual interest. Often found in loafers, you will also see it in certain derbies. The Edward Green Dover is an example of an iconic (hand made) apron toe shoe. Aprons are often polarizing and people love them or hate them.


Allen Edmonds wooster street penny loafer shown with Saphir shoe trees to show what an apron is and what a strap on a men's leather dress shoe is.




11 Popular Dress Shoe Types You Should Know



Cap Toe Oxford 

ZonkeyBoot black calfskin cap toe oxford shoes displayed with Saphir shoe trees


Details: A cap toe Oxford is aptly named. It is an Oxford with a line across the vamp that separates the vamp from the toe cap. This line can sometimes be an extra piece of leather that covers the whole toe cap. Sometimes it can be as simple as a single line of sticking. It depends on the brand and model.


Due to the sleek simplicity of this model, it is very striking when worn. A popular style that you can find from many different makers. It is often found made on pointier more shapely lasts. As always, this will vary. Very well suited for simplicity and dark colours. It can also be found in all different leather types. Cordovan, suede, calfskin, etc. This is a staple for any man that finds himself wear suits at least semi-frequently.


In suede, a cap toe oxford can make a tremendous brown dress shoe as well.


Formal or Casual: More formal


When to wear it: Suits mostly. A black cap toe Oxford is the best choice for a black suit. Darker cap toe oxfords look great with dark suits. A dark brown cap toe Oxford with a navy or charcoal suit is a very smart choice. Choose a more aggressive last if you want to wear it with a more structured suit.


Wingtip Oxford 

Hiro Yanagimachi Wingtip oxford in dark brown suede

 Photo courtesy of Hiro Yanagimachi.




Details: This is similar to the cap toe Oxford. The difference being that these have a “wing tip” pattern on the front. This pattern is denoted by middle point on the toe that points towards the laces. From that point the pattern swoops away from the laces before curling back around and coming back to towards the laces again. This is named because it is meant to resemble a set of wings when looked at top down.


Since a wingtip literally has more going on that cap toe, it is a bit more casual. It can still be a properly formal shoe. These look especially handsome in brown where you can spot more of the details. If you're after a more interesting brown dress shoe, this is a great choice for you.


Formal or Casual: More formal


When to wear it: Like most Oxford these are best with suits. A dark(er) brown wingtip Oxford with a an earth tone or charcoal suit looks wonderful.



Plain Toe Derby

Prada brown calfskin plain toe derby shoes  displayed with Saphir shoe trees



Details: This is one of the most “formal” of the casual shoes. It is fairly plain, given the name. No medallion, brogues, toe cap, or wing tip. This is a fairly unadorned and unassuming shoe. The derby means that it is a touch on the casual side. Since this shoe is so plain, it straddles the line between formal and casual.


The shape of this shoe will be very important. A plain toe derby on a very soft, forgiving, and round last will look more casual. Especially if done in a more textured or casual leather. Think suede or pebble grain. A suede plain toe derby is a fantastic choice for wearing with denim.


Contrast that with a shapely, aggressive last in a dark smooth leather and you’ve got a more formal shoe. A shapely black or dark brown cordovan plain toe derby could be dressed up to wear with a suit.


This style is open to all varieties so choose the one that is best suited for you.


Formal or Casual: Either or, depending on the leather and shape. Leaning on the casual side.


When to wear it: Depends on the make up. We like this style when made casual. Textured leathers in soft shapes. Browns especially. Wonderful with denim, sport jackets, and knits.


Short Wing Derby

Crockett & Jones Pembroke short wing blucher in walnut grain.  Displayed with Saphir shoe trees


Details: This is like the wingtip Oxford above. Two main differences. First is that this is a derby. So it has the additional flats for the laces.


Second is that this is called a “short” wing given on how the wing tip pattern extends. On a short wing, the wingtip pattern extends back roughly 1/3 of the shoe. Ending somewhere near the beginning to middle of the laces. Short wings often has more brogueing and detailing in the middle of the shoe. Where the flaps begin for the laces.


Crockett & Jones Pembroke short wing blucher in walnut grain.  Displayed with Saphir shoe trees


All of this simply adds more visual interest and weight to the shoe. This makes even more casual than something plain. More stuff = more casual.


These look wonderful in brown shades. They can also work in almost any leather type. Calfskin, suede, cordovan, it doesn’t matter. All bring something a little bit different to the table. This is a striking shoe that likely has the most going. It is a popular option for people who want a casual shoe with a little extra. As you can tell by now, there are tons of styles that can be considered a "brogue shoe".


Formal or Casual: Casual.


When to wear it: Great to be worn with denim. A dark brown short wing derby paired up with a dark denim and an earth toned sport jacket or knit is a great look.



Long Wing Derby

Alden 975 long wing blucher derby in #8 shell cordovan Crockett & Jones Pembroke short wing blucher in walnut grain.  Displayed with Saphir shoe trees


Details: A long wing derby is similar to the above. The difference is the wing pattern. A “long” wing has that pattern start at the toes and wrap all the way around the shoes. It meets up at the back near the heel. This creates an interesting side profile. The winging/brogue adds visual interest in a very uniform and sleek way around the shoe. It creates an effect of elongating the shoe a bit.


(Whereas the short wing has the exact opposite effect since it breaks up the shoe half way around).


Alden 975 long wing blucher derby in #8 shell cordovan showing what a long wing shoe is Displayed with Saphir shoe trees


This is an extremely popular and good looking style. A long wing Blucher can come in all different leather types. Often seen in leathers that have a bit more visual interest like suede, cordovan, or grained leather. Alden’s 975 might be the most popular long wing Blucher in the menswear community. Often found in snuff suede or #8 shell cordovan.


Be mindful of the shape when choosing this style. If you go with a more aggressive shape you will find yourself with a slightly more formal shoe. We find this style looks especially good in softer more rounded shapes. Especially the Barrie last from Alden, which looks great for casual shoes.


Formal or Casual: Casual


When to wear it: In a dark colour and an interesting leather, you can wear this very often. This looks especially great with denim. A dark denim, a OCBD, and a dark long wing Blucher is an iconic trad look. It can also be worn with knits and pairs wonderfully with sport coats. If you are looking for a casual wear work horse, this is a great choice.


Tassel Loafer

Crockett & Jones Cavendish tassel loafer in polo/snuff suede displayed with Saphir Shoe trees 

Details: This is a loafer (a slip on without laces) with a set of tassels on the vamp near the instep. The type of tassel can change drastically. Some large, some small. Some are fancy with many elements and some are simple ties. A tassel loafer can come with or without an apron. It can also be made on almost any last shape. The tassel strings can extend all the way to the heel of the shoe. Sometimes down in a visible way, sometimes not. Some tassel loafers will also have an another apron on the shoe at the heel to add more visual interest.


This is an iconic shoe that is often polarizing. Many people associate it with an older and more dated style.


We feel the opposite. A tassel loafer might be the most versatile of shoes you can buy. The leather and shape will make a large difference. A slightly softer shape tassel loafer in a mid to dark brown can work with almost anything. They look equally at home with a suit or with a pair of jeans. Style is subjective so you must always choose for yourself. We find a tassel loafer the best suited for playing double duty out of all the options on our list.


One of the most iconic of them is the Crockett & Jones Cavendish. Not too round, not too pointy. These come with an apron and a modest tassel.


For a more formal expression a smooth leather is a great option. Calfskin or cordovan. For a more casual option suede or pebble grain.


This is a loafer that is often more associated with a British style of dress. Especially popular with styles that try and mix British Traditional and Italian Casual.


Like all loafers fit is very important. You cannot adjust the fit with laces in any way. Your shoe either fits or it doesn’t. Ensure you find a last that works for you.


Formal or Casual: Either or.


When to wear it: In the right configuration you can wear tassel loafers with almost anything. A black calfskin pair will look amazing with dark suits. A chocolate suede with denim and a sport jacket.


Penny Loafer

Allen Edmonds Wooster STreet Penny loafer in dark brown calf displayed with saphir cedar shoe trees


Details: This is a slip on loafer with a strap across the vamp. The strap across the vamp will often have a small indent/slit in it. The small slit originated from a time with payphone. The idea was the keep a penny in your shoes so that you could always have change to use a pay phone in case of an emergency. Different times indeed. (https://magazine.brooksbrothers.com/penny-thoughts/)


A penny loafer can be either “full strap” or “half strap.” On a half strap penny loafer (more common) the strap covers the top of the shoe at the vamp. It stops at around the opening for your foot. On a full strap loafer that strap extends down to the sole of the shoe. A small difference. The full strap loafer’s strap breaks the smooth lines from the side of the shoe. This makes the loafer appear a bit shorter and more stout. Which you should wear it totally up to your preference. There isn’t a functional difference.


Penny loafers also usually have an apron toe.


Allen Edmonds Wooster STreet Penny loafer in dark brown calf displayed with saphir cedar shoe trees apron and strap dispalyed


A penny loafer is an older style that is often associated with more of a “trad” dress. Americana, Brooks Brothers, OCBDs (Oxford cloth button downs). As with anything, there are modern interpretations of it.


Because of how simple and sleek these loafers can be they are good at being formal or casual. The styling will make a big difference. If it has a sot apron, a soft strap, and more shape, then it can be more formal. If it has a very chunk apron and strap, and is on a soft round last, it will be casual.


Formal or Casual: Depends on styling. A bit of both.


When to wear it: Formal penny loafers in dark leathers look at home with suits. Casual softer shapes in more casual leathers look great with sport coats and with jeans.




Monk Straps 

Hiro Yanagimachi Double monk strap men's leather dress shoes made in japan hand made

 Photo courtesy of Hiro Yanagimachi.



Details: The monk strap is a style denoted by a metal buckle used to fasten the shoe. Monk straps opened up or tightened by a leather strap that crosses the vamp of the shoe and is fastened in a buckle. Think like your belt, or a pair of Birkenstocks. Monk straps can be single, double, or triple (or other variations but these are 95%+ of them). The refers to how many straps there are. The most popular are single and double. You can see triple monk straps in certain boots because there is more space. Anything more than that is generally overkill.


Monk straps can be see with or without a toe cap as well. With a toe cap is more popular. They are made in almost every type of leather.


They are a sleek and versatile style. They have been around for a very long time. Given their very unique look, they often oscillate between being “in” and “out” of fashion. We think they can always look good if done well.


Like the tassel loafer, if you’re looking for a shoe to perform some double duty then this is a great option. Generally speaking a single monk is considered a bit more classic. A double monk would be considered more modern. A triple monk would be seen as more of a statement piece.


Due to the somewhat binary nature of monk straps fastening method, they can be harder to fit. Unlike laces where you can always adjust them monk straps usually only have 2-4 holes per strap. Like being in between holes in a belt you can be in-between holes on monk straps too. Keep this in mind when looking to purchase them.


Formal or Casual: Depends on styling. A bit of both.


When to wear it: Given their fairly minimal make up and metal buckles they are very versatile. As always, which leather and shape you choose will make a big difference. A black calfskin single monk strap will look sharp with a suit. A double monk strap in navy or snuff suede will be at home with denim and a sport coat. Or with knits.




Chukka Boot

 Alden chocolate dark brown suede chukka boot on rubber sole



Details: A short boot with a long and plain vamp. Usually with 2-4 eyelets and about ankle height. This is essentially a plain toe derby shoe that extends up a little bit higher and covers the ankle. Usually several inches shorter than a normal “boot.”


This is an extremely popular and versatile style. It is available in almost any shape and almost any leather. Many brands offer several options for it. This is one of the most flattering and versatile shoes you can own.


The simplicity of this boot is what makes it so beautiful. The long and unadulterated vamp lets the shape and texture of the shoe shine through.


Formal or Casual: Either or depending on styling. Leaning into the casual side of things.


When to wear it: A suede or cordovan chukka boot in a dark colour on a softer last looks amazing with sport coats or jeans. Ditto for with knits. They look especially good in the fall winter. They give the look for more weight than a shoe without all of the heft of wearing a boot. A smart choice for very casual suiting or dressing down a sport jacket.


Conversely a smooth and chiseled chukka boot like the Crockett & Jones Tetbury can look smart with a more formal outfit.


Chelsea Boot

Hiro Yanagimachi calfskin men's leather chelsea boot

 Photo courtesy of Hiro Yanagimachi.



Details: A Chelsea boot is a very iconic boot. This is a slip on boot that has as long and unadorned front. No laces, brogues, medallions, etc. Simple a long expanse of leather. To help put them on they will often have elastic fabric gussets on the sides. Sometimes they will have zippers instead, though this is much more rare. These can come in many different shapes and all different leather types. 


This is a popular style given its simplicity and ease of wearing. They are easy to put on and can be dressed up or down depending on the styling you choose. 


Formal or Causal: This greatly depends on your styling. Most often they are a bit more casual. However, compare this pair of Blunderstones to the Chelsea boot from Hiro in the photo above. Night and day difference. A sleek, shapely Chelsea in a smooth leather with a high shine can be a smart formal option. You could even dress it up enough for a suit at times. A rugged, rounder Chelsea on a texture leather and a chunky rubber sole will be very casual. Choose whats best for you. 


When to wear it: A Chelsea boot is most popular in a semi-formal kind of setting. Think of a dressed up denim and button down shirt. Or a pair of trousers with a sport jacket. They are fantastic in the fall and winter, though can be worn year round. I usually recommend something a touch more on the sleek side. The sleekness of the style lends itself wear to a slightly more shapely last. A rugged Chelsea, say from Viberg, will work better in a workwear type environment. I recommend you choose something firmly in one camp or the other. If you try and get something you “can dress up or dress down” then you find yourself stuck in the middle with a boot that isn’t quite at home anywhere. 




Wing Tip Boot

Crockett & Jones Islay Boot in dark brown pebble grain


Details: Almost always a short wing, this is the wing tip Blucher of boots. Like the short wing Blucher, there is a lot going on. Usually you will see a wing tip pattern with a medallion. Brogueing will often extend onto the eyelet flaps and all the way up the shaft of the boot. You will often see extra brogueing on the heel of the boot.


This is an iconic style that has been around for many years. A boot can be an amazing piece of footwear for the fall winter. All of the visual elements added to this from the brogues and wingtip pattern can make it look heft and chunky. In a good way. This heft lends itself to layering and more textured outfits. Think knitwear, outerwear, accessories.


A dark brown pebble grain wing tip boot was worn by James Bond in Skyfall (The Crockett & Jones Islay, as pictured above). Bond wore it with denim and a waxed cotton Barbour jacket.


Alden makes several popular versions of this in suede and shell cordovan. All of these would be a fantastic compliment to jeans. The chunkier version of this style lend themselves to more of a “work wear” aesthetic. Flannel shirts and raw denim.


You can also find sleek version of this in smooth leathers. We prefer the textured leather options. The weight of the style lends itself to a leather that matches that. A very formal and polished smooth leather in this casual style can sometime be neither fish nor fowl. That is to say its not really formal OR casual, so you find yourself stuck in the middle.


Many boots come with a rubber sole. Dainite is popular for more sleek options. Vibram for more rugged.


Formal or Casual: Casual


When to wear it: Very much at home with a pair of jeans. Especially if you get a more casual leather such a Chromexcel (CXL). The texture of suede and cordovan also work well with denim. If you get this style with a simple and smooth calfskin you will want to wear it with dressier denim options or proper pants.




Who Makes Good Shoes?


Ranking anything can be difficult to do. There are many factors that contribute to the quality of something. Not the least of which is perception and personal preferences.


Some people obsess over the minutiae of what makes something the best. Searching evermore for a marginal increase in theoretical quality. In reality the differences between great and top 10 aren’t massive. The biggest thing you want is to reach is some sort of quality minimum threshold. (That’s not to say the search can’t be fun. Only that it is limited in its practicality). Going from a terrible shoe to well made shoe is a massive jump. The different between Steve Madden and Crockett & Jones is night and day. The difference between Alden and Edward Green is noticeable and drastically smaller.


Given that, I want to give people who are interested something to refer to. I will list some big names in the game. I will not be ranking brands. This list will be far from exhaustive. If I miss one of your favourite brands that you think deserves a mention let me know. These brands vary dramatically in their scope. Some of these smaller Japanese makers might produce 10-100 pairs of shoes a year. Allen Edmonds might make that many in an hour.


Some of the brands we have listed are very high end. Hiro Yanagimachi, for example, along with some of his Japanese contemporaries are making some of the best shoes on the planet. These are the top 1% of whats available on the market. Calling them artisans is more apt than shoemakers. 


The term “leather” is a bit nebulous and can vary in quality drastically. Genuine Leather is something you see all the time. Genuine leather can be great or it can be terrible since its such a blanket term. Leather terminology is only one item to look for.


Quality and fit > quantity. If you have a smaller budget to work with you might be better suited to approach some of the high end options 2nd hand. Well made shoes can last a long time and thus can be found previously worn at a much more approachable price. Often you can find 2nd hand shoes in great shape simple because the fit didn’t work out for the first buyer.


Not surprisingly the low end brands are the lion’s share of the market. A general rule of thumb will be to avoid companies that try to compete exclusively on price. Companies that don’t have a history of quality. If their shoes are available in mass quantities that is a bad sign. Good shoes are difficult to make and take a long time. That's why you can’t find high end labels stocked on shelves in 12 different stores per city nation wide. If it’s available in a strip mall store that has many locations across your city, your odds are worse.


Lastly, keep in mind that high price doesn’t mean high quality. Some large fashion labels offer shoes so that they can offer entire outfits. If a company specializes in clothing and seems to have expensive footwear as an add-on, the quality can vary dramatically. For example, Canali makes superb clothing. Their footwear, in our opinion, is not of the same quality. Especially for the price point. Other fashion labels like Prada and TOD’s aren’t seeking high quality either. This may or may not be a bad thing. You might not need the highest quality shoe (not everyone does). Sometimes you’re going for a certain look. Nothing wrong with that. Simply know that you can find a better made shoe at a lower price. It is up to you to determine the value proposition.


Also note that where a shoe is made is not the end all be all. That is to say there will be good and bad product coming out of anywhere. To Boot New York is made in italy. So is Stefano Bemer. They are leagues apart in their quality. Perry Ellis and Allen Edmonds both have models made in the USA. They aren't made the same.


High end shoes will be shoes that are well made. They will have some type of stitched/welted construction offering. They can generally be resoled. If treated well they’ll last longer and feel better than lower tier options. They will be more expensive than the lower end options. They will often look better as well. On higher end models more attention is paid to the last and the shape of the shoe.


Luxury models will be some of the top end offerings. These will usually be hand made, hand welted, and/or bespoke. These will be some of the better or best options available. If you want to treat yourself. Keep in mind that a high end sports car isn’t more expensive because it’ll last longer than a Honda Civic. It’s expensive because of the experience it offers. The same is true for ultra premium shoes. The person spending $5,000 on a pair of bespoke shoes likely has a large shoe rotation. Those shoes get infrequent use. They’ll likely never wear out (let alone even need a resole). Some people think that experience is worth the price. It’s up to everyone’s individual tastes.


So below is a list of makers that we feel make good shoes. Shoes worth purchasing. Price points and styles vary. Quality will vary between this list as well. All of them are “good enough” without a doubt.


One note before continuing. Allen Edmonds used to be a sure fire shot for a quality shoe. Many people look to Allen Edmonds as their first “nice” pair of dress shoes. This can still be the case. However not 100% of their models are made in the USA anymore. They’ve outsource some of their construction to Italy and the Dominican Republic in some cases. The quality of the leathers, in our experience, aren’t what they were 10+ years ago. Do they still make some great shoes? For sure. Make sure you look into which model you’re after though. Their classics still seem to be made well and in the USA. Some of their more seasons and stylish options, it’s case by case. Allen Edmonds is also easy to find on the 2nd hand market. If you buy from their website they have lots of good stories of quality customer service.


If you’re looking to dip your toes in for the first time (no pun intended) it can be a bit daunting. Allen Edmonds (ideally on sale), Meermin, and Yanko are probably a good place to start. Those will give you a reasonable product for the price. They are likely the most entry level on this list. I’ve read many accounts that Meermin can have a long and harsh break in period though. Be mindful.




A Few High End Welted Shoe Brands To Look For


Alden, Allen Edmonds, Barker, Bontoni, Buttero, Church’s, Corthay, Crockett & Jones, Edward Green, Enzo Bonafé, Foster & Son, Gaziano & Girling, George CleverlyHiro Yanagimachi, John Lobb, Meermin, Nick’s Boots, Saint Crispin's, Stefamo Bemer, Vass, Viberg, Yanko, Yohei Fukuda, Zonkey Boot.




Shoe Care


We’ve written extensively on the details of shoe care on this blog. We highly recommend you read through if you’re looking to make your investment last. If you’re new to the game, we recommend our beginner’s guide. If you’ve polished your shoes before then you might be interested in some of our more specialized posts


Also be mindful that if you went out and got yourself a well made pair of shoes, you'll want to use premium shoe care products. Protect your investment. A jar of polish lasts a long time and will do wonders. 


A brief outline on the basic elements of shoe care.


1. All leather shoes need moisturizing.


Leather needs to be moisturized from time to time. No matter what type it is. Your hands dry out and can use some lotion. Shoes are the same. You should be using a highly nourishing leather lotion on your shoes 3-6 times a year. More or less depending on how often you wear them. And in what type of conditions. And no, Saphir Renovateur is not enough solely on its own.


2. All shoes can benefit from brushing.


Regularly brushing your shoes is extremely important. It removes surface dirt on all shoes. It helps bring a bit of a shine back to smooth leather shoes. It helps align the nap (hairs) on any type of textured shoes like suede or nubuck. Brushing your shoes with a horse hair brush is essential. If you can brush your shoes for 10-20 seconds after each wear it will go a very long way for your shoe health.


3. All shoes can benefit from shoe trees.


Shoe trees do tons of your shoes. They help them last longer, reduce creasing, and minimize odours. They are the most overlooked and underrated elements of shoe care. We highly recommend a pair of each pair of shoes you own. They should be in your shoes whenever your feet aren’t.


4. Rest your shoes.


Wearing your shoes on back to back days is damaging for them. The leathers in your shoes are absorbing all of the excess sweat and moisture from your feet. Over a day this can really add up. Wearing them back to back doesn’t give the leather time to dry and reset between wears. Even if you have a pair of handmade $5000 Japanese Bespoke shoes, you shouldn’t be wearing them daily. Paying more doesn’t mean they can take this type of beating. You wouldn’t drive a Ferarri in torrential weather simply because you paid more for it.


5. Shining your shoes goes a long way.


A little bit of cream polish on smooth leather from time to time does wonders. It can add colour back into your shoes. Fill in scuffs and nicks. It can really rejuvenate your footwear. We recommend Saphir Pommadier Cream Polish. Use it every couple of weeks or months, depending on wear. Or whenever your shoes look tired. Whichever comes first. Wipe your shoes with a damp cloth to clean them. Apply a small and even coat in circular motions all over your shoes. Wait 5 minutes for it to absorb. Buff to a shine with a horse hair brush and that’s it. This is likely enough to give you the best looking shoes in the office. 5-10 minutes a month.





This should give you an overview of some popular shoe styles. We also touched on styling and when to wear what. You should now understand the essential elements.


This guide is not exhaustive. Nor is it prescriptive. Part of the fun of fashion is doing things your own way. Having your own take on things.


By understanding the basics and having a good feel for the rules of the game you can know when you want to break them. When you want to step outside of the lines. And how.


Let us know how your style and footwear journey has changed over the years. Or maybe how it has stayed the same. Let us know in the comments below.

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We totally agree! If you’re on your feet often (which many of us are) having quality footwear goes a very long way. It is much better in all ways. They are better for your feet, they look better, and in the long run better for your wallet. While fine footwear has a high upfront cost, the cost per wear can be very low with good maintenance and care. Not to mention you get the joy of wearing beautiful and comfortable shoes every time you put them on.


This page content is really helpful because if we need to start something in our life related to our fitness then we need to select good quality shoes.


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