Here’s what articles about the best dress shoes for men usually do:
They list X number of shoes and hope you’ll buy any of them so the site owner can get a cut of the sales profit.
Every time I come across an article like that, I wonder:
‘Where’s the advice on dress shoe colours? or
Which type of footwear is right for me?‘
The thing is:
When it comes to finding the best men’s dress shoes, everyone has different needs, so why give the same broken advice?
‘Buy $250 black dress shoes, and you’ll be fine.’
BTW, that advice is complete B.S.
With that said, this is your lucky day …
… because in this article I’ll give you the missing puzzle pieces you need to buy a pair of dress shoes successfully.
75% of Men Shouldn’t Wear Black Dress Shoes
Let’s talk about black shoes.
Most guys wouldn’t buy anything but black dress shoes.
However, a thing most style coaches don’t tell you is this:
Spring and autumn men should only wear black dress shoes with a navy suit on ceremonial occasions.
If the occasion is just dressy (as it usually is)…
… they should wear brown dress shoes instead, as brown is a much more flattering colour to warm seasons.
As for that other 25% of the guys:
The best dress shoes for summer men are burgundy.
Summers can wear black shoes, but burgundy goes with everything in their palette. Black, on the other hand, should only be worn with summer’s darker greys, cool browns, and navy.
Only winter men get full value from the ‘universal’ black shoe advice, as everything in their wardrobe looks stunning with black dress shoes.
The 5 Best Dress Shoes for Men
We’ve established your best dress shoe colour, but what about the shoe itself?
Which are the top shoes for men for dressy occasions?
The term ‘dress shoe’ is too vague to work with, as there’s more than one type. And not all styles are equal — not even by a long shot.
Some are dressy enough to wear with a tuxedo …
… while others are best worn with jeans or chinos.
Let’s review the five best dress shoes for men:
Instead of laces, monkstraps have one or two buckles on the outer side. These buckles secure a piece of leather that’s folded over the tongue of the shoe.
As you can see from the picture, monkstraps, or monks, are based on open-lacing shoes, where the sides of the shoes are sewn on top of the vamp.
The most popular colour for monks is black; however, if you’re a spring or autumn man, stick to brown.
Monkstraps dress shoes also come in one and two buckle models.
- The monkstrap’s design makes it easy to fasten and unfasten the shoes.
- Two-buckle monks are very comfortable, because they distribute pressure more evenly across the instep than one-buckle monks or lace-ups with four or fewer eyelets.
- Hems that fall onto the shoes can snag on the buckles, making them drape unattractively. To avoid this, you should always wear tapered pants with monkstraps.
‘Suede’ refers to the material only, not the style. Suede shoes include loafers, Derbies, brogues, and occasionally Oxfords.
With a few exceptions, black suede shoes never became popular. Today, suede footwear is mainly available in brown.
Suede shoes are considered casual, but that’s not exactly true. No, suede footwear isn’t appropriate for offices with a formal dress code or ceremonial events such as weddings and funerals, but …
… suede IS excellent to wear with jeans, chinos, or suits. With jeans and chinos especially, the soft look of napped leather creates a great contrast to the rough twill fabric in the pants.
- Suede leather is usually more affordable than waxed leather.
- Suede shoes are available in practically every style.
- Suede doesn’t cope with water as well as the other best dress shoes for men. With that said, a little water won’t hurt it, as marks can easily be removed with a wire brush.
After Derbies, these are probably the easiest to recognise of the five best dress shoes mentioned in this article.
Brogues are Oxford shoes with embellishment of various degrees.
There are four different types of brogues, listed below from dressiest to least dressy:
- Quarter brogues have decoration along the rim of the toecap, upper, and heelpiece only.
- Half brogues have a decorated toecap and decoration along the rim of the upper and heelpiece.
- Full brogues, or wingtips, have a toecap with decoration that extends back along the sides to the middle of the shoe, creating what look like wings. These shoes also have decoration along the sides of the upper and heelpiece.
- Longwing brogues have a toecap with decoration that extends and wraps all the way around the heel of the shoe. In addition, the upper also has decoration along the rim.
NOTE: I haven’t been able to find an image of long-wing brogues in the closed-lacing Oxford style — only in the open-lacing Derby style.
If the brogues have open lacing, this should be made clear by the shoe’s name, as in ‘quarter-brogue Derbies’, ‘half-brogue Derbies’, ‘wingtip/full brogue Derbies’, and ‘long wing Derbies’
- If you’re used to wearing casual shoes, brogues provide a softer transition when switching to dress shoes.
- Brogues are also widely available and look great with jeans.
- With the exception of quarter brogues, brogues are too busy for sleek fabrics. That’s why they should be reserved for jeans and flannel or patterned trousers.
Oxfords are the most formal of the best dress shoes for men mentioned in this article.
With their closed-lacing style, they simply look more elegant and formal than Derbies and monkstraps.
A true Oxford should have a toecap, but be aware that …
… Oxfords are not the same as quarter brogues, even though they look very similar.
Black Oxfords are some of the most popular shoes, which is great since they’re the best leather shoes to wear with your navy suit to business events and formal occasions. Black is also a big plus for winter men, because it means the shoes can be worn with trousers and chinos as well.
If a spring or autumn man wants to don Oxford shoes with jeans or other pants …
… he should opt for brown or burgundy for summers. That’s because these men should wear black shoes only with a navy suit.
- Oxfords can be worn on all formal occasions, which means you don’t have to worry about footwear for your next business presentation or wedding invitation.
- Oxford shoes are too formal to wear with anything other than dress pants, trousers, and chinos.
In my opinion, Derbies are the best business shoes and best dress shoes for men.
Their open-lacing design and clean look make them perfect for any semi-casual or dressy event.
If your occupation doesn’t require you to wear Oxfords, then Derbies are the only dress shoes you’ll need. (If you need Oxfords for a special occasion, wedding companies rent them out.)
Although finer models have five eyelets, four are more common and do the job just as well.
Derbies, or bluchers, come in a wide variety of colours and leathers. Plain, solid-coloured shoes are, however, your best option.
Toe decoration is also common on these shoes. If you want a classic look, choose a regular toecap or plain toe. However, if you want to stand out, apron and split toes are common.
- Derbies are the most common dress shoe, so they’re easy to get hold of.
- They come in virtually every colour, which makes it easy to pair Derby shoes with a suit or any other outfit, regardless of the occasion.
- There aren’t many disadvantages to Derbies; the only possible downside of these best dress shoes for men is that they can be too casual for truly formal occasions.
Alternative Shoes That Are Missing From the Best Dress Shoes for Men List
Did you notice any shoes missing from the list of the five best dress shoes for men?
I’ve wilfully left a few types of footwear out.
However, since I know many of my readers are truly interested in knowing everything there is to know about shoes, I’ll give some shoe types honourable mention here.
I mentioned loafers in my article “Best Casual Shoes for Men: the 5 Best Types and Colours” but the thing is:
Not all loafers are casual.
This makes it hard to classify loafers as good dress shoes, because they’re not — with two exceptions:
- Gucci loafers have established themselves as a versatile classic. You can wear these with any smart–casual outfit, suit, or tuxedo.
- Tassel loafers have broken free from their ‘casual shoe’ label too. These are now generally acceptable business wear in the U.S.
Spectator shoes are wingtips with a contrasting toecap, heel cap, and sometimes lacing panels. Today, spectators are regarded as quite old-fashioned and harder to pull off than regular wingtip brogues.
Since this article focuses on the best dress shoes for men, I’ve left boots out. But I should mention that on dressy occasions when the weather is against you, you’ve got boot alternatives.
Closed lacing boots (dress boots), Chelsea boots, and open-lacing boots can all be worn with trousers, chinos, and jeans.
The Best Dress Shoes for Men Have These Important Signs of Quality
Full-Grain, Top-Grain, Nubuck, or Suede?
Although it can be hard to tell what type of leather your shoes are made of, you should know that leather quality varies considerably.
Full-grain leather is the highest grade.
Only the outermost part of the hide is used (grain). The leather remains strong and has its natural surface intact, so the hide can’t have any scrapes, scars, branding marks, or visible defects. Therefore, full-grain leather sells at a premium.
Top-grain leather has had the outermost surface removed.
This is typically done to blemished hides. The sanded leather surface is pressed and refinished to look like full-grain leather. Top-grain leather is weaker and less durable than full-grain leather is.
Nubuck is top-grain leather that’s sanded for a plush texture.
If you want a plush look and feel but want something better than suede, Nubuck is the answer. Since most of the grain is left intact, Nubuck is stronger than suede — which is reflected in the higher price. Even so, Nubuck must be treated similarly to suede.
Genuine leather is the leather that remains when the grain is removed.
This is the cheapest part of the leather used in shoes. It’s stronger than canvas but not as strong as full- or top-grain leather. Left untreated, genuine leather is called ‘suede’, but it can be refinished to look like full-grain leather.
The Worst Leather: Wet Blue, a Sign of Poor Quality
Most shoe leather is what we call ‘chrome-coloured’.
Acids and chrome salts strip the natural hair, fat, and oils from the raw hide, leaving behind what is know in the leather industry as ‘wet blue leather’.
Without any further processing, this wet blue leather would rapidly crack and deteriorate, since no original oils remain.
Tanneries have to tan the leathers to restore colour and nutrients, making the leather soft and durable. The problem is that the colouring chemicals are expensive and the process is time-consuming, making leather expensive.
But some tanneries can create cheap leather by cheating.
They colour the leather just long enough for the pigments to penetrate the outer surfaces, so the leather appears dyed. But if you look at the edges, you will see a telltale blue centre.
This blue core is the wet blue leather, which requires a lot of maintenance to keep from deteriorating.
On most shoes today, the edges are concealed or painted. If you have the chance to inspect the edges of a promising pair of dress shoes, make sure that the centre isn’t wet blue, but dyed all the way through.
Soles and Sole Stitching
I’ve touched on this before: not all soles are equal.
Personally, I prefer dress shoes with rubber soles, because they leave me with one less thing to care for.
If you fancy shoes with a leather sole, I have to hand it to you …
… they’re way classier than rubber soles. However, leather requires more TLC than boring rubber. Just remember: even the finest leather soles have rubber on the heel.
There’s also different ways of attaching the sole.
On the cheapest dress shoes, the manufacturer simply cements on a rubber sole and hopes it sticks until the warranty period expires.
The best dress shoes for men have soles that are stitched on in one of two ways:
The upper is stitched straight to the sole through the insole.
This makes for a very slim and flexible shoe …
… but since the stitches go through the outer sole, water can seep into the shoes. Thus, blake stitching is useless if you live in a rainy climate.
It may not come as a surprise to you that blake-stitched shoes are common in sunny Italy, but not in damp Great Britain.
The upper is first fastened to a welt, which is then fastened to the sole.
The extra welt makes the sole look a bit lumpier. However, since the stitching doesn’t pierce the inside of the shoe, your feet will stay dry, even if you step in a puddle.
Well-crafted shoes have layered leather heels. Each layer is called a ‘lift’, and it usually takes three to five lifts to achieve the correct height.
On shoes with rubber soles, the bottom lift is usually made of rubber instead of leather …
… but even shoes with leather soles have a piece of rubber where the heel gets the most wear.
I still remember when I bought my first true dress shoes.
As I tried on different pairs in the shop, I felt ridiculous, looking down at pointy-toe shoes. They were such a contrast to the sneakers I had worn for the first 20 years of my life.
That’s the thing:
The best dress shoes for men aren’t sneakers. They’re in a completely different league …
… and consequently, when buying your first pair, you might have to literally step out of your comfort zone.
The toe shape most rookies feel comfortable wearing is actually the worst shape out there.
I’m talking about squared-toe dress shoes. They were a fashion fad in the ’90s, but some stores still sell them.
Okay, so now that you know which toe shape to avoid, let’s look at your actual alternatives:
Pointy, round, and squared-off pointy-toe shoes
- Round toes are the safest choice if you’ve never worn dress shoes before. This classic shape is also widely available, making it perfect for your first buy.
- Pointed toes are the complete opposite of round toes.
As the name suggests, the toe tapers to a point — great if you have narrow feet, but other than that, I don’t see a reason why anyone would wear such shoes.
- Lastly, we have something in between: squared-off pointed-toe dress shoes. Some of the best dress shoes for men offer this toe option.
Like round-toe shoes, squared-off pointy shoes come with plain, cap, split, and apron toes. However, cap and plain toes are the most popular.
For anyone who’s serious about their dress shoes, squared-off pointed toes are the best-looking option.