Ultimate Guide To Dress Shoes – The 5 Types Of Shoes You Really Need

Women Know Best

What do you think is one of the first things that women first notice about a man? Do you think it is a well-trimmed beard? Or maybe that you match colours well and are wearing an outfit that is well put together. While all of this is true, if you have nailed all these parts of your outfit it will be in vain if you have neglected one of the most important parts: The dress shoes.

Women and people that know the details will always look at the shoes. I can feel those laser eyes scanning me in the street when I walk. Even if you have a well ironed shirt, pressed pants and a Hugo Boss suit it is game over if you are wearing square-toed shoes.

Just No.

Grab a cup of tea and relax because this is going to be a long guide. It will cover all the different kinds of dress shoes out there and help you make a better, easier choice when you go shopping in the sea of dress shoes. If you are impatient skip to the bottom of the page and read the summary. What I do promise is that after reading this guide, you will be able to choose the best type of shoe for the occasion and understand the subtle differences.

The Most Important Investment You Will Ever Make

Dress shoes are arguably one of the biggest, costliest and most important purchases a man can should make. You might think that it is a luxury to have a great pair of shoes, just because you never wear a suit. I beg to differ. It is a necessity. As Captain America said, there is going to be a time to “Put on the suit”. In any part of life fortune favours the bold but even more importantly favours the prepared. My days in the Special Forces taught me that it is important to be a step forward so you do not fall 2 steps back.

For the man looking to build a complete wardrobe there are 5 types of shoes needed. The occasion is what dictates which one you need. I really like this quote by Tom Ford because it showcases the power of the correct dress shoes.

Never do business with a man in loafers”.

For the average man starting to learn about fashion and style, this could be one of the most important articles to read.

Won’t I Save Money If I Buy A Few Cheap Pairs Of Dress Shoes?

Return Of Investment

The situation is the same with many of the items that we buy. We often think that we can buy a few pairs of shoes, shirts or other utility items that are cheaper (and subsequently lower quality) because our budget is small and this way we save money. That is not the case when you think long term.

Let me give you an example.

You buy a cheap pair of shoes, say around 50$ because you cannot afford those 300$ dress shoes. They look fine in the beginning, but after frequent wear they deteriorate quickly and in just a year, the glued sole falls apart and you need to get new ones. This will happen even faster if you wear them more frequently.

In just 6 years you will have spent 300$ for dispensable shoes, while the better quality ones with proper care and an easy resole will last you potentially decades. This is a good return of investment.

Pro Tip: Instead of investing in a cheap pair of dress shoes, get the best that you can afford. It will increase both your confidence and your looks and you will get much more mileage out of them.

How Much Should I Spend On Dress Shoes Then?

No matter if you are the type that will wear them once a year or every day I would advise spending minimum 200-300$ on quality dress shoes. You will thank me later.

I remember when I first wore R.M. Williams Chelsea Boots and how the leather hugged my feet. What a feeling it was, like being protected and naked at the same time. Freedom.

And the compliments. You will get compliments from strangers, coworkers, women and possibly jealous mean comments by male friends. That means you are doing something correct my fellow gentleman.

Thanks Misiu Academy! But What Do I Look For In A Dress Shoe?!

Quality dear reader. You look for quality. But as always, remember that a premium brand name does not equal high quality or the money. In dress shoes the quality of the leather and the craftsmanship are most important. A few pairs of good dress shoes are better than 10 low quality generic pairs.

Pro Tip: Subscribe for free in the brands that interest you and you will receive free newsletter with promotions quite often. You can save a lot of money for a superior pair of shoes. Paul Evans for example has amazing and frequent discounts if you are in the USA.

I Get It Now! But…What Is High Quality?!

This is exactly why what this article is about. To help you understand in everyday language the differences between dress shoes and the hallmark of a quality pair.

The construction of the shoe and the leather quality is what distinguishes a cheap shoes from an expensive shoe. Here are a few things to look for when buying dress shoes:

  1. Look for real leather. Good leather will develop character over time, mould itself to your feet after every use and have a beautiful patina. In simple terms, leather is like wine, it gets better with age. Leather has a grading system, depending from which part of the animal it comes from. The hierarchy is counted in grades. Full Grain (Grade 1) > Top Grain (Grade 2) > Genuine Leather (Grade 3) > Belly Leather (Grade 4) > Bonded Leather (Ungraded). For a detailed explanation on this, read this amazing article by Hugo Jacomet.
  2. The quality of the stitching. What did we say when we discussed how to buy your first suit? It also applies here. Look for little details, such as inconsistencies in the stitching that reveal cheap craftsmanship.
  3. The sole type. I will not go into much detail about this in this article, but always avoid glued soles. They will break fast and the shoe is worthless. The other two main types of sole stitching are blake stitch and goodyear welt. The goodyear welt is generally more expensive but also higher quality and allows for a much easier resole process.
  4. Check the inside of the shoes. Is the lining synthetic? Leather is a sign of higher quality.

Mini Summary

• Try to buy dress shoes made from calfskin instead of cowhide.
• Goodyear-welted shoes are more expensive but have easy resoling and will last longer.
• Avoid glued soles and synthetic materials.
• Stitching and the inside of the shoe reveals quality craftsmanship.
• Practice by comparing how a cheap shoe looks and feels to touch against a high quality one.
• Leather sole is more formal, but it is worth getting a good rubber sole if you live in colder climates with snow.

Fantastic! Now I Feel Ready To Know More About Dress Shoe Types!

You are a hero if you have read this far. There are a few types of dress shoes but for simplicity’s sake I will narrow them down to four: Oxfords and Derbies, Monk Straps, Loafers and Dress Boots.

When it comes to the style, the less detail on the shoe, the more dressier and formal it is. Here are a few examples that apply mostly to Oxfords and Derbies:

  1. Wholecut: Made from a single piece of leather. Usually more expensive because of the precision and quality required. In my opinion it is the most beautiful, elegant and dressy shoe a man can have.

    Beautiful elegancy by Carlos Santos.

  2. Plain Toe: No details, your go-to formal shoes for any occasion.

    Carlos Santos Derbies – Plain Toe

  3. Cap Toe: Same as above, with a little more character on the toe line. It is very acceptable to wear in the higher echelons of business attire.

    Löf and Tung Oxfords – Cap Toe

  4. Brogues: Is it a style, an expression or a category of its own? It is up to you to decide. These perforations on the shoe are called “brogues” and come in different formats. Generally, the more broguing on the shoe, the less formal it is.

    Löf and Tung Oxfords – Brogues

The Oxford and Derby Shoes

The Oxford Shoe is the pinnacle of formality when it comes to dress shoes. In male formal fashion, the simpler a shoe or the suit, the more formal and elegant it is. The oxford shoe has a long history as at timeless formal piece of footwear, gaining traction and popularity from the University of Oxford in the 18th Century. When you wear a suit, an oxford will be always the most perfect fit and look classic. What defines the oxford shoe and distinguishes it from the derby is the closed lacing vs the open lacing. On the oxford, the flap (or eyelets) are stitched under the vamp, giving a sleeker, uniform and dressier look. On the derby the lacing is open, which means the flaps are stitched over the vamp.

Additionally, because of the black tie formality, the darker shades are also more formal when it comes to dress shoes. A black oxford is the pinnacle of formality.

The Derby shoe is accepted in business attire and you will see it very often in business casual environments. Broguing is often encountered but in my personal opinion I prefer shoes without broguing. They are comfortable and a great choice for frequent everyday wear. They are very often mistaken as oxfords by people that do not understand the simple difference described above, so here is a picture of my own shoes that hopefully explains it once and for all.

Left: Loake 1880 Dark Aldwych Brown Oxfords – Right: Lloyd Dark Brown Derbies.

Monk Straps

Monk straps are a very interesting category of dress shoe. It is lower in the formality ladder and is characterised by the straps on the top. The strap can be fastened using a single or double-buckle closure. People would put it between the oxford and the derby in terms of formality but I have personally not invested in a pair so far. I do not find them attractive yet, or better say I would invest in different types of shoes before I consider them.

They can be dressed up with a suit or dressed down with a good pair of chinos or even jeans. They are different than most shoes and they will attract attention. Quite often they will be the focal point of your outfit, so be careful with what you want to project or if you want to make a statement.

Paul Evans Double Monks

The Loafer

The loafer is a slip-on style of shoe in the lower parts of the dressing hierarchy, though I have seen some dress it up with a suit. It is a moccasin style of shoe with different styles on the top, most notably the penny loafer and the tassel loafer. Penny loafers have an old history and got their name because wearers used to stick dimes in their lip-slots on the top to make calls from phone booths in the 40’s and 50’s since mobile phones were not invented back then. The tassel loafer has *surprise* a tassel on the top which makes it stand out. Personally, I would not wear loafers with the suit and I feel that the tassel will make me look like a door or a curtain. I am not ready to see myself in them yet.

Paul Evans Loafers

Dress Boots

Dress boots are essentially oxfords just with a longer shaft. If you are tired from the sea of normal dress shoes and want a change, a good dress boot is an acceptable formal piece and appropriate for formal day wear. I currently do not have sufficient experience with them and I prefer Chelsea Boots.

Magnanni Cap-Toe Boots

Chelsea Boots

Ah, the Chelseas. Originating from Victorian England and popularised by the Beatles, the Chelsea boot is an elegant and flexible dress shoe. It has a slip-on style at ankle height and usually is a plain toe. They have a stretch panel and if they don’t: They are NOT a Chelsea boo.

Chelsea boots are so flexible they can be dressed up with a suit and break the monotony while still looking sleek and classy or dressed down with jeans and a dark polo shirt.

I would say they sit just below the derbies in terms of formality, but they are perfect for any occasion and everyday use.

My own Loake 1880 Chatsworth Chelsea Boots

Chukka Boots

The Chukkas are casual, plain toe boots with open lacing that got their name from Polo. A chukka is a unit of time and lasts 7 minutes. They are shorter than the Chelseas and reach up to the ankle. They are often made from Suede and are appropriate for casual wear. It is not appropriate to wear them with suits.

Paul Evans Chukkas

Special Mention: Suede

Suede is a type of leather that has a rough feel to it and looks very distinctive. It can look very beautiful and is often seen in Chukkas, Chelseas or Monk straps. Suede does not like water, so I would stay away from them if you live in an area where it rains a lot (Hello my Sweden!).

Carmina Oxfords in Suede

So Which 5 Types Of Shoes Should You Invest In First?

Remember, the darker the shoes, the more formal they are. The same applies to decoration and details. Here are the first 5 types of shoes you should invest in first.

1) A Black Oxford Shoe

If you never wear formal shoes and you need to have just one pair, then buy a Black Oxford Shoe without any broguing. Plain-toe or cap-toe. Whether you have to attend one black-tie event, a wedding or a funeral, keep them polished and they will never fail you. Perfect for any business environment.

2) A Brown Oxford Shoe or Derby

Same as above, only slightly less formal. Shades of brown go with virtually everything and will make a great match with chinos, dark jeans or a navy/grey suit. Perfect for business, everyday use and can be dressed down with jeans. People will start to look at you differently. Having brogues is a personal preference and perfectly acceptable. They are good to develop your own style and work well in a more laid-back office environment.

3) Brown Chelsea Boots

Now that you have the most important categories covered, it is time to experiment a bit. Try a pair of brown Chelseas (or Black if you like wearing grey colors). They are comfortable and after a long day in the office, they are the perfect shoes to wear for a night out. They look great in Suede, but avoid it if it rains a lot in your area.

4) A Pair Of Wholecuts

Wholecuts ooze elegance and finesse. They are not a requirement, but once you have the basics, a pair of wholecuts will elevate your style to a new level. They will accompany you to any event and they will turn some heads. Do not use them every single day though, as they are made from a single piece of leather and creases tend to show much easier. The colour is a personal preference, but I like dark brown and oxblood shoes. Here are my dream shoes from Carlos Santos.

5) Loafers/Monk Straps

Here is a category I have not explored yet but one that I can see good value in. Monk straps can make a statement and used frequently, while loafers can be worn in the office or when driving for more comfort and prolonging the life of your dressier shoes. They are perfect for warmer climates and loafers allow you to go sockless (or with no-show socks) for added comfort.

Time To Wrap This Up

Wow! Today we learned about so many new things and drank a lot of tea to go through them. I hope you enjoyed reading the content and like my personal style of youthful writing. If you do, I would be delighted to see your comments. You can also subscribe by using the form in the right so you do not miss any new content.

Here is a quick final Summary:

• A man really needs 3 types of dress shoes, that extend to 5.
• The less details on the shoes, the more formal they are.
• Oxfords have closed lacing, Derbies have open lacing.
• Shoes are the most important investment.
• Black is the most formal colour, followed by dark brown and lighter shades.
• Suede is not optimal for rainy climates.
• Goodyear-welt shoes are easier to resole and last longer.
• Leather has different qualities based of the part of the animal they come from.
• If you buy square-toed shoes, wear sandals with socks or hang out with Poly and Ester, I am going to hunt you down personally.

With all that being said, I hope you enjoyed one more article. In the following weeks, we are going to go through my personal collection of shoes, how to match shirts, ties and patterns and possibly go through some brand showcases that I trust and use.

Thank you for reading,

Kostas Mandilaris,
Misiu Academy

Written by Kostas Mandilaris