Dress Shoes: The Final Piece Of Puzzle In A Man’s Wardrobe

We’ve heard this before, that shoes are the anchor to one’s outfit. So why do so many men still skimp on dress shoes when they spend tonnes of cash on bespoke suits? Whether you realise it or not, shoes are integral part of your suit. So getting a right pair to coordinate with your outfit is crucial.

Window display of a shoe shop, showcasing various types of dress shoes.
Many types of dress shoes for the many different combinations of a man’s attire for many different occasions.
Image by Pexels of Pixabay

The Different Types Of Men’s Footwear

We’re not going into the comprehensive history of footwear. You can read about the history and evolution of footwear here. What we’re gonna discuss is more about the different types of shoes, and how to match them.

There are generally two categories of shoes – functional shoes and dress shoes. Functional shoes are, well, less form and more function. That means, they’re more of a tool than a decorative piece. Dress shoes, as their name suggests, is part of a dressy article to complete one’s outfit. Of course, both categories have the primary purpose to protect one’s feet. But that’s about the only commonality that they share. So let’s take a look at the differences :-

(1) Functional Footwear

We can further breakdown functional footwear into several sub-categories, depending on their specific purposes :-

  • Safety shoes/boots – To protect one’s feet from external force. Usually comes with steel capped toe box and anti-slip soles. These are standard issue on factory floors, construction sites, and any other hazardous work areas.
  • Outdoor shoes/boots – To protect one’s feet, and sometimes ankles too, from the uneven surfaces of the outdoors. You can further break these down to specific uses for specific shoes/boots. Hiking/jungle boots, climbing shoes/spikes, ice cleats, Wellington boots, etc.
  • Training shoes – To absorb shocks and protect one’s feet from strenuous sporting activities. You can further break these down into specific sporting activities for the specific shoes. Tennis shoes, sprinting spikes, football boots, golf spikes, basketball boots, running shoes, etc.
A pair of safety boots, showcasing the ultimate protection of one's feet in the toughest environments that they have to work in.
A typical pair of safety boots, Note the heavy-duty leather construction, complete with steel toe box to protect the toes from being crushed. And the soles are made of thick anti-slip rubber, reinforced with steel plate to prevent puncture by nails.
Image by Steve Buissinne of Pixabay

I’m pretty sure I’ve left out many others examples, but you get the drift.

(2) Dress Shoes

For the lack of a better elaboration, well, dress shoes are just that, dress shoes. Its main purpose is to coordinate with one’s outfit. They span from ultra formal footwear all the way down to casual attire. And by “casual” I don’t mean sloppy… The formality of one’s outfit determines what footwear is a suitable match. There’s no clearcut description, there’s only a guideline as to the “sub-categories”. And these sub-categories are :-

  • White/black tie formal – The highest level of formality in one’s outfit.
  • Business formal – board meetings, formal presentations, award ceremonies, etc. This covers most of the formal business events.
  • Business semi-formal – business meetings, corporate functions, business lunches, etc. This covers everything but the most formal business events.
  • Business informal – business meeting at country clubs, outdoor business activities, client entertainment, etc.
  • Business casual – dress down Fridays, after-hours meeting at the bar, date night, etc.
  • Casual – when you’re at home, with family, or during private times.
Combination of garments that are laid out flat to make a complete casual outfit.
A typical casual outfit, consisting of patterned, light coloured shirt with a dark tie, dark wash jeans and khaki sport jacket. And the whole outfit is anchored with a nice pair of casual Oxfords. Whilst Oxfords and dark brown colour are pretty dressy on its own, the burnished toe, contrasting sole, stitching and laces tone down the formality of the shoes by a fair bit.
Image by Benjamin Rascoe of Unsplash

Again, there’s no clear-cut description as to what shoes matches which outfit. But there is a guideline for each outfit. Each type of footwear is usually acceptable for a range of sub-categories. And to complicate things even more, they can sometimes overlap one another too.

Different Types Of Dress Shoes

To make things easier to comprehend, we look at formality as a linear scale. On one end is the most formal, and the other end the least formal. Thus, the general consensus on the formality of dress shoes is as follows :-

  • Colour – Black shoes are most formal, followed by dark brown, medium brown, light brown, tan, and then only other colours. The darker the colour, the more formal it is.
  • Material – Smooth leather is the most formal, followed by textured leather. A rule of thumb is the coarser the texture, the more casual the shoe is. Picking up the last place in formality is nubuck/suede. Here’s a link to find out more about the different types of leather.
  • Decorations – The more decorations there are on the leather, the more casual it is. For example brogues, tassels, medallions, mismatched colours/textures, etc. Hence, the least decorated pair of dress shoes are the most formal pair.
Toes of two types of dress shoes, one with a plain toe, and the other with decorated with a medallion.
The left shoe has an undecorated toe, as compared to the right shoe that’s decorated with a medallion on the toe. The cleaner the appearance, the more formal it is. Hence the shoe with the medallion is the more casual of the two.
Image by Thanh Tung of Pixabay

But the most prominent determining factor for the formality of dress shoes are the shoe design itself. Whilst there are countless types of designs, they can generally be classified into these four types. Here’s the link to the anatomy of a shoe for your reference.

(1) Oxford Shoes

Oxford shoes have a closed lacing system. The lace closes on the extension of the vamp itself. Sewn underneath the vamp is a separate piece of tongue. This clean outline makes it the least distracting, thus the dressiest form factor.

A pair of Oxfords in black smooth leather. This is the most formal of all dress shoes.
This is a pair of black, plain toe Oxfords. Note the vamp is a single piece of leather, with the split pieces of lacing leather that goes underneath the vamp.The tongue is another separate piece of leather, which is then sewn underneath the lacing leather and the vamp.
Image by Free-Photos of Pixabay

Short of the traditional pumps (court shoes) for white/black tie, Oxfords are the most formal. It goes well with white/black tie all the way down to business informal. Of course, the simpler the design, the dressier it is. The clean design of a plain toe Oxford makes it the most formal. Once you start introducing brogues, medallions, etc., it drops in formality very quickly.

(2) Derby Shoes

Similar in construction with Oxfords, with only one distinctive difference, Derbies have open lacing system. With Derbies, the tongue is the extension of the vamp itself. One separate piece of leather on each side of the shoe meets up over the vamp/tongue, and secured by laces. The open lacing system allows more wiggle room, making it more comfortable for the wearer.

A pair of medium brown Derby shoes, showcasing the open lacing system, as opposed to Oxford's closed lacing system.
This is a pair of medium brown, plain toe Derby. Note that the vamp/tongue is a single piece of leather. Two pieces of leather are sewn on the sides of the vamp, and close over the vamp with laces.
Image by Michi S of Pixabay

Generally considered suitable for all business attires, though it’s shun upon by purists. After all, Derbies are inherently less formal than Oxfords. So to be safe, avoid wearing Derbies for your white/black tie, business formal and semi-formal attires. Similar to the Oxfords, the less decorations they have, the dressier it is.

(3) Monk Straps

Similar in construction with the Derby, except that monk straps close with straps and buckles, not laces. Same vamp/tongue construction, and one piece of leather on the inner side, securing over the vamp/tongue. Instead of laces, monk straps secure with a piece of leather strap from the inner side, and buckle on the outer side. This functions more or less like a leather waist belt. The two staple monk strap designs are the single monk, and the double monks. These refer to the number of straps and buckles. Of course there are other rare variations too, like the triple monk strap, but I digress…

A pair of medium brown double monk straps, with cap toe and minimal brogueing. The toe comes with "burnt out" design, with the tip of the toe graduating from dark brown to the medium brown of the rest of the shoe.
This is a pair of brown, cap toe double monk straps. Note that the vamp/tongue is a single piece of leather. A large piece of leather is attached to the vamp on the inner side. This piece flaps over the vamp/tongue, ending in two belt-like straps. On the other side are buckles to secure the straps.
Image by Thanh Tung of Pixabay

Some consider monk straps to be an oddball. In that they’re neither formal nor casual. For that reason, I wouldn’t recommend you to wear monk straps with suits. However, they do match very nicely with business informal outfits. So take them as an alternative to the more common Oxfords or Derbies when you reach for that blazer.

(4) Loafers

Loafers are the lowliest of the dress shoes when it comes to formality. Usually cut with a very wide opening, they don’t really need any closing at all. They’re the typical slip-on shoes, but built like dress shoes instead of functional or casual shoes. Even within loafers, there’s still a difference in formality too. Traditional penny loafers take the top rung, followed by traditional horse-bit loafers, and whatever else trendy designs falling below that.

A pair of penny loafers in tan suede.
A pair of classic penny loafers in tan suede. Whilst the design of the penny loafer is considered pretty dressy where loafers are concerned, the suede and lighter tan colour tone down the formality a fair bit.
Image by Alex Hudson of Unsplash

Though technically still classified as dress shoes, loafers are inherently more casual. I wouldn’t personally wear loafers with a suit. Loafers are the best match for business casual outfits. They’re great for when you reach out for that sport jacket, regardless whether with or without neckwear.

A pair of medium brown horse-bit loafers, showcasing the bronze coloured hardware across the vamp/tongue.
A pair of medium brown horse-bit loafers. Construction wise, it’s pretty similar to the penny loafers. But the addition of hardware (the metallic horse-bit) to the overall leather shoes makes this a rather casual pair of shoes.
Image by Noah Smith of Pixabay

Are White Trainers Alternatives To Dress Shoes?

There are many recent advocates of wearing “dressy” white trainers as an alternative to loafers. As the name suggests, trainers are for training and sporting purposes. So when you’re training for, or participating in sporting events, then yes to trainers. But for the times when you need to layer your outfit with at least a sport jacket, stick to loafers. Remember this, if you have to dress to impress, you complete your outfit with dress shoes, not trainers.

A pair of white trainers. This is the antithesis of the dress shoes.
Yes, that’s a handsome pair of white trainers indeed. But would you want to wear them with your business suit?… I wouldn’t think so. Just keep them to what they were designed for – sporting activities.
Image by Daniel Storek of Unsplash

Shoes Anchor One’s Image

Your choice of footwear completes your outfit. You don’t dress to the nines, only to fumble with your choice of footwear. Your footwear has to complete your overall personal presentation. It’s never an afterthought. You don’t complete your bespoke suit with your bedroom slippers. Shoes are indeed the anchor of one’s image projection. So if you want to project a charismatic personal brand, then make sure you choose the right kind of shoes. And if you need help, reach out to Solarex Imaging. It’s never too late to learn how to project a likeable personal brand.

What about you? Do you have different dress shoes for different dressy occasions? Or are you the same-shoes-for-every-occasion guy? Leave your comments below. But in the meantime, do vote in the poll too.

Do you coordinate your shoes to your overall outfit?
3 votes · 3 answers

About CHOW Wei Ming

Brand consultant, photographer, creative director, storyteller, and a true believer of the power of visual communications. Outwardly expresses a friendly disposition, but hides a perfectionist nature deep inside him.

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