Surprisingly, there is a lot to know about shoes. As a gentleman, you don’t need to know everything, but you should make sure you know a little more than the average person. From different styles to the construction of a shoe, we put together the most important things you should know. Before we dive in, let’s have a look at the anatomy of a shoe. This will help you further understand the terms used in this post.  

What style of shoe am I wearing?


Before we start listing different styles, we want you to grasp the difference between the two most popular styles: Oxford and Derby. A gentleman can’t mistake derbies for oxfords. So here is an easy tip: Look at the laces. As you can see below, one has open lacing and the other has closed lacing. It’s that simple. You are already ahead of most.


Now let’s begin with a list of styles:



The oxford shoe is the most timeless and formal of the dress shoes and a good starting point if you’re looking for a classic staple. These shoes are a very useful option that can be dressed up with formal wear or down for a more casual arena. The oxford shoe is categorized by its face being stitched under the vamp. This is called “closed lacing” as we saw earlier.


The oxford shoe comes with some details you should be able to identify.


The cap-toe Oxford is perhaps the most widespread Oxford shoe style that exists. The most famous color is black and is the most popular shoe for the majority of classic men’s shoe producers. It is also available in brown, tan, cognac, oxblood, etc.


The Wingtip Oxford has a pointed toe-cap with additions called wing-tips that goes along both sides of the shoe.  Though technically an Oxford shoe, it is commonly referred to as a Brogue (will see later). The shoe when seen from above the cap is shaped like a ‘W’ or an ‘M’ depending on the view.


This oxford shoe type has an upper that is cut from one single piece of leather. Normally, most shoes are made from many different pieces of leather sewn together. The whole-cut oxford has the unique closed lacing system and this feature along with the single piece structure gives it a tremendously clean and smooth look. It also needs more leather to make a whole-cut because it generally has only one seam at the heel.


The plain Oxford principally comprises of the vamp and the quarter. It doesn’t have a leather cap over the toe box or a broguing. This oxford type is simple yet sophisticated.



Derby shoes which is also known as the blucher or the Gibson, was initially envisioned as a hunting and sporting boot around the 1850’s. By the 20th century, the Derby shoes became recognized as fitting footwear for the town. Derbies are mostly mistaken as oxfords, as their shape is very similar and their differences are very minor. Although their difference is not noticeable at first glance, it is in the placing of the face of the shoe. A Derby has the facing stitched on top of the vamp while an oxford’s tabs are sewn under the vamp. This structuring called the open lacing gives chance for a wider fit and for many individuals, this makes the Derby shoe a more comfortable choice.


Like the oxford, the derby may have the same details. 



The cap toe derby may or may not feature broguing, though most times, the broguing is normally limited to the edge of the toe-cap but at times you also see medallions. They mostly do not feature heel caps, although some do. The cap toe derby is a bit less formal than a plain derby, in terms of formality.



The wing-tip derby has the pointed toe-cap  which is usually shaped like a ‘W’ or a ‘M’ or ‘U’ with extensions which either goes along both sides of the shoe or stop just short of the heel cap and are then called wingtips. They have broguing both on the edges and in the middle and have heel caps when the wings don’t extend along both sides of the shoe. It is considered the most informal of all and available in several kinds of leathers.



The plain derby comprises of a quarter and vamp and does not consist of any other additions like broguing, cap-toes or heel-caps. It is referred to as the most formal among the several types of derbies and is normally available in black; although no-a-days they come in many other colors.



The Brogue is a style of low-heeled shoe or boot usually categorized by multiple-piece, durable leather uppers with decorative broguing and serration along the pieces’ clear edges. Present day brogues trace its roots to a basic shoe invented in Ireland that was produced using pale hide.Brogues were normally seen to be country or outdoor footwear and not suitable for casual or business occasions, but now, brogues are considered suitable in most contexts. Essentially, any style shoe with decorative serrations becomes a brogue. Below you can see different types of brogues. Can you tell which one is a derby? 


The monk strap shoe appeared as a certified design for the first time in the year 1901 but is more likely to have had its origins 150 years before then. Presently, monk strap shoes are an essential part of a classic gentleman’s shoe collections and double monks have achieved a certain kind of majority appeal. In Mediterranean states mostly, men often wear completely or partially unbuckled double monks to emphasize their nonchalant look.


The loafer, unlike most shoes has many origin stories. One of these is said to be the moccasin, which adds to the confusion. Yet, the two most known, widely-considered and accepted notions are:

1. They originated from a Norwegian man who crossbred traditional Native American and Norwegian footwear.

2. They came from an English royal commission of a new form of house shoe.

Though it may be hard to know the exact source, what is fascinating is the story and journey of its development. The loafer is a lace-less shoe, its ankle is exposed, and they do not wrap snugly around the ankle. It often has a low heel and the upper vamp has a moccasin-like structure. At times, loafers have a piece of leather across the vamp which is known as a saddle.

Here are three types of loafers you should know about.


The Penny Loafer

G.H. Bass shoe company in 1936 presented its version of the loafer, and is known for it till today. The company’s design consists of a unique strip leather of the shoe with a diamond-shaped cut-out. This loafer version was named Weejuns to sound like Norwegians to distinguish them from the Spaulding loafer. The weejuns became very popular in America, majorly among the Prep School students in the 1950s.


The Tassel Loafer

It is still uncertain what the origins of the tassel loafers are. It is claimed that the tassel loafers were famous with the Ivy league set in the 1920’s. Anyhow, we do know they make any man look elegant and sophisticated. Whether at home or on the dance floor.


The Bit Loafer

A bit loafer is a slip-on laceless shoe that has a piece of metal running across the vamp. You may recognize this type of shoe as it was popularized by Gucci in the 1960’s and are still popular today.



These shoes offer a relaxed yet fashionable and timeless look appropriate for everyday wear or something a little more formal. The driving mocs is a contemporary form of the traditional Native American moccasin with the addition of rubber tabs on the sole. This addition supplements to its longevity and versatility while maintaining the flexibility and comfort of a traditional moccasin.


The Opera pumps or court shoes are the plainest formal wear shoes for men. Their model dates back to at least the 1730s at the time when the European noble and gentlemen wore low, delicate, often silken, and lace-less footwear in court and society gatherings. A specific trend was leather soles or heels dyed red. As modern pumps have transformed a little from their forefathers, they are men’s oldest classic shoe type still in use.


The boat shoe also called the Top-Sider and deck shoe has passed the well-compressed path from being purely work or utility wear to becoming a truly classic piece of men’s footwear. With The Official Preppy Handbookpublication by Lisa Birnbach. In 1980, the boat shoe began to be recognized as an essential and basic part of the Preppy style. However, Boat shoes are not just limited to preppies but have been accepted by many people and are a staple in many individual’s wardrobe. Owing to their distinctive design and structure they are not just great for boat decks but the perfect shoes for the summer months.



The Bucks are like the Blucher oxfords. It looks like a dress shoe, but is made of suede and usually has a brick red sole. It initially appeared in the late 1800’s and was proposed to be tennis shoes. The prototypes were made from Brazilian or Chinese deerskin, so it being made from buckskin is where its name was gotten from. The bucks’ red sole was presented in the 30’s and the white buck was made famous by Pat Boone in the 50’s. A great shoe for a more casual look.


Chukka boots also share a few similarities with Jodhpur and Chelsea boots.  The name ‘Chukka’ is derived from the game of Polo and so linking them, however slightly different from the Jodhpur boot that was made particularly for Polo. In the modern day, the Chukka boots have become far more versatile than the originals and have been stylized to suit the times. The changes in the finer style details of the boot these days determine if they are suitable for business or leisure.


Chelsea boots have Victorian roots. The invention and design of the boot is ascribed to Queen Victoria’s boot maker J. Sparkes-Hall. However, he would not have been successful without the development of vulcanized rubber. It has rounded toes and low heels. It has two parts each made from a single piece of leather: the vamp and the quarters. The elastic strip extends to just down the ankle but not all the way down to the sole. Although Chelsea boots have their first 4 characteristics with the Jodhpur boots, the remaining 3 differentiate them from the Jodhpur boots.

How Were My Shoes Made?


A gentleman must understand the basics of shoe construction, knowing how a shoe was made and the processes it goes through, so that he can know how to maintain it and recognize a good quality shoe when he sees one.



The Cement Construction which is also known as stuck on construction is used for flexible and light-weight shoes and the outsole is fixed to the upper by adhesive. Most shoes are made this way as it is inexpensive and fast. This type of construction is less durable and of lesser quality than the others. You can easily identify a shoe made with glue by looking at the bottom of the shoe to see if there is stitching. If not, the outsole was likely glued to the upper. 


The Blake-stitch also known as Veldt is a cheaper but more durable technique used to make lightweight flexible soles. In this method, the upper, the insole and the outsole are stitched together from the inside of the shoe. This way, you don’t see any stitching on the top of the shoe but you see it on the bottom as you can see below. This contruction makes quality shoes at a reasonable price.



The Goodyear Welt is used for highest quality shoes, the top section is chain stitched to the upper and insole rib at the part where it curves under the last. The Goodyear Welt creates thicker/heavier less-flexible shoes and the process is regarded as the toughest of all shoe constructions. One way to identify a goodyear welt is to look at where the upper and the outsole meet. There should be a layer of leather (welt) stitched to the sole. As you can see below, there is stitching on top of the sole and under.

What Materials Are My Shoes Made Of?


Men’s shoes are made with different materials like leather, rubber, suede and many more. Knowing what your shoe is made of can give you a better understanding of its features, help as a big indicator of quality and necessary ways to care for your shoes.



Leather is the most used shoe upper material to produce work boots and work shoes. It has several qualities that make it one of the best components for shoe making like breathability, moisture absorbency, customization and durability.



The Suede is just like any other leather. When treated well, it lasts longer but if not maintained well, it will get ruined. The suede when used to produce shoes gives a sophisticated and stylish look.



The use of rubber for shoe soles are normally sub-contracted to a factory that focuses in the compounding and pressing of the rubber parts. You will find shoe makers use rubber soles for added grip and flex. 



This material provides the shoe designer a huge variety of textures, colors and features at a range of prices.  Though synthetics materials were once seen to be cheap and not appropriate for high quality shoes, times have changed; these synthetic materials are now high performance and are mostly a combination of two layers.  

When purchasing a shoe, you really get what you pay for. If you try picking out cheap shoes with thin soles, you will end up buying a shoe that not only looks cut-rate but might wear out quickly. You should buy a shoe that will last you years, if not decades, making the amount of use you get out of it exceeds the price.


Good quality shoes are all about production and design, and there are few important things to look for:


The shoes should be made of real leather and have leather soles as well.

A well-made shoes’ sole will be stitched, not glued, to the bottom of the shoes.

Also, the linings in better shoes are made of quality natural leather or calfskin, not synthetic materials.

Lastly, check out the stitching. It should be neat and should be barely noticeable.


What Color Of Shoe Should I Wear?


Nothing makes you look more stylish and give you a confidence boost like a nice pair of quality shoes. Every man should have a few pairs of great dress shoes for the inevitable events that will call for them. But also, every man needs to know how to match these shoes with the right outfits.

What you wear on your feet can break or make any look. It actually doesn’t matter if you have the best suit in the world because if you have bad shoes, you might as well just roll in a puddle of mud. When choosing a shoe for an occasion, you should be mindful of colors, knowing which color is suitable for your wear or which is not. Black shoes tend to be more formal and brown/tan/cognac shoes are a little more relaxed. Brown shoes are especially good in the summer with lighter color suits. Try to wear black shoes with a black suit and brown shoes with gray and blue suits. If you want to spice things up, burgundy shoes look great with jeans and a blazer. 


Caring For Your Shoes


Once you know you have a quality pair of shoes, you are going to want to take good care of them. A quality pair with good care can last you over 20 years. Here are a few shoe care tips:

-Shine your shoes regularly

-Clean your shoes regularly to remove dirt, stains and scuff marks

-Use moisturizing cream to nourish the leather and keep it from cracking




There you have it. You now know what you should know. Go ahead and analyse your shoes and see if they are oxfords or derbies, cemented or stitched, and next time you make a shoe purchase you’ll know what to look for. Like a true gentleman.