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Know Your Men’s Formal Shoes | Vintage & Modern

When it comes to formal shoes, most men think that there is just one type. The formal shoe (lol). We tend to oversimplify classifications of footwear because, aside from colours, only minor details distinguish them. We need to talk (at least once) about men’s formal shoes.

Knowing how to classify and distinguish them; when to wear them and in combination with what, are some things we need to know to avoid making mistakes with them.

And what about vintage/retro models? How do they look? Can they be worn even today?

In this guide, we provide you with the necessary background knowledge on everything about formal shoes. How to distinguish them and what sets apart the vintage/retro models from newer ones.

Be sure to check out our shoes review post to know more about some of the best footwear available online.

For a better understanding of the terminology used in this guide, please refer to this image of the shoe’s anatomy

Oxford Shoes

black oxford shoes

When men referrer to formal shoes they are usually talking about oxford shoes. Also known as Balmorals (some say the shoes come from England, others from Scotland), these shoes are the pinnacle of formality.

They are usually worn in working environments, weddings, dinners, and many other formal events, although they have the unique trait that they can be worn casually too.

Two golden rules: 1: With footwear and clothing in general, casual wear usually can not be worn formally, however, the inverse is valid (formal can be worn casually). 2: With all shoes, the cleaner the pattern and the darker the colour, the more formal the shoe is.

Oxfords are characterized by their ankle exposure; closed and leather lacing, that is, the eyelets are attached under the vamp; their low heel, and finally their broguing depending on formality (see brogue shoes).

Vintage models tend to be leather-made but newer models can be made out of other leathers, faux, suede, and canvas.

More important, oxford shoes are a series of shoes with the above traits in common but with small differences between them.

The Plain toe is the one most people are familiar with. This is because…. well, it is plain. No broguing, leather caps, or any other fancy decoration.

This type of shoes are ideal in business environments as they combine perfectly with suits, however, they can still be worn casually with blazers and trousers for example.

plain blackk oxford shoes

Plain Oxford

Vintage models are easily identified by their eye-catching sewing, sometimes even a little worn off. They also tend to fit a little more loosely and they go great with non-slim pants.

vintage oxford shoesVintage Plain Oxfords

The Cap toe is also widely popular and it features a straight and sharp front. These shoes look longer than the plain toes, and they have a distinctive division near the toe due to an extra piece of material added at the edge.

Try to wear them to business environments and very formal events, however, they are slowly being accepted in formal events with more strict rules, like the black-tie events. Outside formal environments, they are great casual shoes in combination with, for example, jeans and a dress shirt.

In vintage models, the division might be a little more flashy and the shape might be a little more rectangular (not as smooth or curvy as recent models).

vintage cap toe shoesVintage Cap Toe Oxfords

The Whole cut oxfords are made entirely with just one leather piece that covers the whole shoe, hence the name. These shoes are more discrete and maybe slightly brogued, also, they are seemed along the heel, although seamless shoes are a thing too (they are more expensive). Overall, the whole cuts are ideal for the most elegant occasions.

Modern Whole Cut Oxfords

Although also relevant for other shoes, the main difference between a modern whole cut and its vintage counterpart is the leather. Advances in technology have allowed us to have more colourful, better-feeling, and thin whole cuts than before. Still, a vintage model wins when it comes to uniqueness, details, and durability.

Vintage Whole Cut Oxfords

Finally, the brogue shoes are also part of the oxfords but we go into more detail down below; for now, let’s move to another very popular footwear.

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Derby Shoes

The Derby shoes are the smart/casual counterpart of the oxfords. They feature an open lacing (the opposite of the closed lacing) meaning that the eyelets are stitched on top of the vamp, and thus, it is seamless between the tongue and the shoe’s front.

Derbys also have a wider range of adjustment than oxfords, potentially making them more comfortable.

Wearing Derbys with a full suit might not be the best idea as these are less formal than the oxfords. Most people don’t notice the difference but for a trained eye, they will definitely look out of place. Try some trousers, a rolled-up dress shirt, or a sweater with them.

You can find some ideas in our relaxed elegant outfits of our formal vintage outfits post.

Just like the oxfords, there a wide variety of Derbys, some of which we have already discussed.

The plain toe, cap toe, whole cut, and brogue shoes are all derby shoes too.

The plain derby is considered the most elegant out of the bunch, the cap toe does not (generally) feature heel caps and may/may not be brogued, the whole cut (some consider this a blucher shoe but still we put it here) is adapted with small facings laid on so the lacing goes over, and the brogues… we talk about them soon 🙂

Not present as an oxford we have the round toe which, as its name suggests, has a round front. It usually comes with a higher platform and it is great for casual combinations of slim trousers and long coats among others.

Round Toe Derby Shoe

Other models not as popular as the ones mentioned above are the white buck, spectators, apron toe, Norwegians, split toe, each of them having unique traits that listing them all will deviate your attention. We encourage you to dig deeper into these if you want to become a derby shoe guru.

As for vintage models, it is common to find divisions or broguing different than the usual ones, more attention to detail, and thicker and more resistant materials.

Vintage Derby Shoes

Blucher Shoes

Another open lacing shoe that is commonly mistaken with the derby is the blucher shoe.

Distinguishing between the two can be kinda difficult and at first glance, it may seem that they are the same, however, the difference lies in the way they are laced. In the Derbys, the lace is due to the quarters sewed to the vamp, while on the bluchers is due to small leather pieces sewn on the shoe.

Bluchers are thicker and more resistant than other formal shoes.

Like with other types of shoes, we have plain and brogue bluchers. Just like the Derbys, in combination with casual/smart outfits and clothes like trousers, jeans, jackets, etc… the bluchers go great.

What is the vintage look of a blucher? A boot! The blucher comes from a military boot used during the mid-XIX century. Modern boots are more delicate and thin, so if you want to try a more traditional look, go for the thin and robust ones.

Blucher Boot

Brogue Shoes

We finally get to brogue shoes! Broguing refers to the small holes that are pinched into some part of the shoes as decoration.

Depending on the abundance of the holes and the location, you can have different types of brogue shoes.

Quarter brogues have the least amount of holes, with only the toe cap and the edges perforated. Semi brogues (half brogues) have all the quarter brogues’ perforations plus some more at the cap’s center. Full brogues or Wingtips on the other hand are almost entirely perforated with a characteristic silhouette close to a “w” shape.

Brogue types (Image by

As we said before, broguing reduces formality; the more you have, the less formal your shoe is.

Quarter brogues are formal enough to wear with a suit, semi brogues might be ok with suits but go better with smart casual outfits, while wingtips are entirely smart casual. Country outfits are ideal for brogues.

So how do vintage brogue shoes look?

Really old models are perforated all the way through; this is because the hole was originally designed to let water out. Another vintage trait is when the shoe is made on a commando sole under a derby upper. Vintage brogues tend to be brown-ish.

Styles like the welted sued brogue or the brogue boots were very popular during the last decades of the XX century.

Vintage Brogue Shoes

Monk Shoes

Over the last century, the original footwear of medieval monks was transformed and adapted to modern necessities, thus giving birth to the monk shoes.

One of the most adaptable formal shoes out there, as business environments, smart casual, casual, are all ideal for monk shoes (just remember to be discrete when going fully formal).

The monk shoe is leather made, low-heel, and features a buckle or buckles in the case of double buckle monk.

Vintage models can be identified by bigger or rough buckling, as well as “older” leathers used.

Vintage Monk Shoes


Our last dress shoe is the loafer, a classic low-heel, leather shoe, that resembles a slip-on.

Loafers can be Penny loafers, which have a plain leather band crossing the vamp; Bit loafers, which have a metal band crossing the vamp; Tassels, which have a tassel attached to the leather band crossing the vamp.

Loafers require you to choose your outfit more wisely. Slim outfits go better with them, as loose ones tend to overshadow them and erase their formality.

Still, they are very comfortable and a great alternative to traditional formal shoes.

You will never again misuse formal shoes!

Now that you know the main types of formal footwear, both vintage and modern, and have a general idea how to wear them, there is no excuse for not looking great every time you go formal 🙂

If you wanna know more, in the future we will do some cover some outfit alternatives for these shoes, as well as doing some reviews on the best options available online.

We hope you have a great day and don’t forget to leave your comments down below. Your opinion is of much interest to us!


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6 thoughts on “Know Your Men’s Formal Shoes | Vintage & Modern”

  1. I got quite an education on the different kinds of shoe categories there are. I was surprised when you mentioned that formal Oxford shoes can also be worn in a working environment. I assume you mean in an office, and not working in construction for example. My introduction to formal shoes was when I got my first tuxedo. Known as dinner jacket and trousers in England. It looked like the Oxford design in the first picture and was constructed with patent leather. 

    Can I assume that formal shoes can only come from the Oxford category and not the others? 



    1. Hey Edwin! Formal shoes are not restricted to Oxfords. Whole cuts, Derbys, and even (slightly) brogue Derbys can be formal. Traditionally only Oxfords were allowed in the top formal events, however, in recent years standards have been relaxed up to the point that the shoes I just mentioned are accepted too. It all depends on how strict the environment is. Just remember that formality goes like this: Oxfords – Wholecuts & Derbys – Brogue shoes.

      Thank you for your comment!

  2. I was surprised the first time I heard loafers referred to as casual. Today it’s common to consider them on both sides even though traditionally they are dress shoes. For me, formality is a spectrum: between two pairs of shoes, there will always be one that is more formal than the other.

    1. Hi Abel! Indeed, formality can be interpreted by comparing two pairs of shoes, so for example, the loafers are more formal than a pair of sneakers. Still, I would suggest determining formality based on the occasion/event (it also determines the rest of the outfit), that way you will always nail the look, which ultimately is what we want.

      Thank you for commenting!

  3. A very interesting post.

    While I was fully aware of these types of shoes, I certainly didn’t know the depth of knowledge and background that you have brought us.

    Personally I like the brogues, as I like a little bit of design on the toes, rather than the plainness of the oxford.

    I thought you made a good statement when you said that you can dress down a shoe, but you can definitely not dress up a casual shoe.  That is very true.

    Thanks for sharing.

    1. Thank you for commenting Geoff! The rules of dressing up/down a shoe is something that is so simple yet many people overlook it. Glad to know you found the article helpful!

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