You’re on a first date.
Dressed to impress.
Trousers are pressed, the shirt is ironed, and the details are on point!
She arrives grinning from ear to ear.
And then looks down and sees them…
Your cracked, 10-year-old, square-toed leather shoes.
Dress shoes can make or break your outfit, gentlemen.
They're arguably the most important investment a man can make in his closet.
Luckily, you only need 5 pairs of dress shoes to upgrade your shoe game.
Read on to find out what they are.
#1 – The Black Leather Oxford
The first shoe you should start with?
Black Leather Oxfords.
The sleek simplicity makes the Oxford the perfect choice for formal occasions.
A pair of formal black oxfords will carry you through the most formal of events – black tie, weddings, funerals and job interviews.
The difference between an Oxford and a Derby is the closed lacing system – the bottom of an Oxford shoe's lacing section is sewn closed.
The shoes should be made of box calf leather and it should not have any broguing. Oxfords are the best worn with business suits and professional attire, but not suitable for casual occasions with jeans or khakis.
Keep in mind that the Oxford is a dress shoe – purchase a pair with leather soles and be sure to shine your Oxfords thoroughly to prevent them from dulling.
Whether you are wearing a tux to a black-tie event or a business suit, these minimal shoes will complement and add a dose of formality to your attire.
#2 Brogue – The Brown Leather Brogue
A footwear staple for the contemporary gent.
Originating in the marshy bogs of Scotland, brogues were initially designed with real holes to drain out water. The traditional perforations on the shoes upper – the brogueing – gives the shoe a distinctive character that other smart shoe styles lack.
What’s so unique about the brogue is its versatility.
A shade of light brown can be limiting because it tends to look strange with dark suits. A medium to dark brown pair can look great with any suit color except black and will still work with chinos or jeans
Although a brown wingtip brogue is ideal, leather brogues in tan, chestnut or chocolate all work seamlessly with your wardrobe, allowing you to create the maximum number of outfit combinations.
Traditionally, brogues are less formal than oxfords. Consider them for work, especially if you work in a laid-back office. These shoes are suitable for outfits ranging from smart to smart-casual. Full brogues can be worn with outfits ranging/ from the formality of a three-piece suit to a casual pair of jeans.
For a smart casual and comfortable, yet refined look, wear them with a white button-down shirt and rolled-up dark denim jeans.
#3 – Slip On (Loafer Or Monk) – The Suede Loafer
Moving down the formality scale, a loafer is a slightly more casual shoe. The laceless silhouette features an elegant design that makes the loafer a highly versatile style, right after a leather brogue.
The slip-on loafer was originally designed as a house shoe for King George VI. Loafers offer the ideal silhouette for going sockless, making them the choice of footwear in warm weather locations.
Penny loafers are the most popular choice although if you were stranded on a stylish European island with just one pair of shoes to wear every day, a pair of brown double monk straps would be an excellent choice!
#4 The Leather Lace-Up / Slip-On Boot
If you have already secured yourself a quality pair of oxfords, brogues and loafers, the next pair of shoes in line to complete your shoe selection is a pair of leather dress boots.
Smart leather boots are rugged and dressy, making them a versatile choice to complement just about any look. Your options range from semi-casual lace-up boots to dressier slip-on Chelsea boots.
- Leather Brogue Boots: This is a boot that works with suit trousers as well as with jeans. Wear them for a dressier take on rugged.
- Lace-up leather boots: Crepe-soled desert boots are a popular option but they add a casual touch to your outfit.
- Chelsea boots: The Chelsea is a slip-on style, like the loafer, with an elastic ankle that makes them flexible and comfortable. These are the perfect boots for a day at the office that extends into a night out on the town.
Leather boots can be teamed up equally well with tailored jackets during the work week as with a pair of jeans and a T-shirt at the weekend.
A pair of rugged leather lace-up boots, ideally with rubber soles will keep you sure-footed in rough weather.
#5 Wholecut Leather Shoes
This one's a wildcard. They are not a required item in your shoe wardrobe in terms of functionality, but in terms of elevating your style.
Wholecut leather shoes exude pure elegance through a minimalist, narrow shape, with clean lines and a smooth surface.
The upper (the leather that is visible above the sole when a shoe is worn) of a wholecut leather shoe is constructed from a single piece of leather. Wholecuts are made using a flawless piece of skin, ensuring high-quality leather. A great deal of expertise and skill goes into making a pair of wholecut shoes, a fact that is reflected in the relatively high cost of these shoes.
Probably the dressiest shoe you will own, these versatile high-quality leather dress shoe can accompany you through your entire day.
Wear them from the office to a dressier evening event or pair them with a pair of smart jeans.
Now, you can go out and buy a $100 pair of men's dress shoes and you wear them once.
Or you get yourself a nice pair of $350 shoes and you wear them 350 times.
Which of those ended up a better deal overall?
Dress shoes are one of those items that you want to invest a little more in.
Even though a good pair of men's dress shoes will be expensive, getting the right ones in the right order will return your money’s worth, especially if you take care of them.
All right, here's a look at the 5 men's dress shoes we believe are essential and in what order you should get them.
Let’s get into the first pair of shoes that you want to own.
We’re talking about Balmoral Oxfords.
These will work great when wearing a suit and that’s what you want from your first pair of dress shoes.
You can wear them to a wedding or to the office – basically any time you’ve got to wear dress shoes.
When you're getting dressed up, you want to look your best – so you need to have that pair of shoes that will work with it.
Black is going to be the “go-to” color for a lot of guys.
It’s got the elegant look with a closed lacing system, I recommend the whole cut or cap toe.
But be careful, even though you’ve got closed lacing on this pair of shoes, we start to see a little bit of broguing.
So, once you start getting into cap toe broguing, all of a sudden the formality of it is starting to go down.
You could still pull it off with a suit, it just becomes more casual.
Next, we have Bluchers.
They look similar, but the big difference here is going be an open lacing system, that’s the key differentiator.
You’ll find that these shoes, in general, are going to have broguing or ornamental stitching – and more often than not they are going to be in lighter colors.
So, these are going to be your more casual men's dress shoes.
You can still pull it off with a suit, but they’re going to look better with dark wash jeans. You can always dress them up with a pair of flannel trousers or regular dress slacks – maybe with a sports jacket.
These are going to be very versatile and I think should be the second pair of shoes in a man’s wardrobe.
3. Slip-On (Loafers or Monk Straps)
Let’s have a look at the slip-on shoes.
There is a wide variety to chose from.
The reason I love slip-on is that they’re casual and comfortable.
When you are traveling, they're very easy to take on and off to be able to go through that metal detector at the airport.
Then we have the Monk Strap – which is not technically a slip-on but I'm putting them here because you don’t have to lace anything up – which I personally love.
I personally like to go with darker men's dress shoes.
Then we have the Tassel Loafer and Penny Loafer.
These are going to be a little bit less formal than a monk strap, but I find many men pull these off effortlessly with a sports jacket.
You can wear them with jeans and it’s going to look great or if it’s in a very dark color, such as black, you can even pull it off when wearing a suit casually.
Then we have the driving shoe, a variation of the Moccasin.
These are not something you want to wear walking around too much – they have a rubber sole that might wear out quick.
But if you want something that you can wear around in your car or you want a nice slipper for around your house, these are going to work great.
Now, to add a bit more fun, you can always go for a suede finish on your shoes, it's going to give a more casual feel and bring a bit of personality.
4. Dress Boots
The fourth shoe style that I’m going to talk about is the dress boot.
Let's start with the Chukka.
It comes out of England. It started as a wartime desert boot, it has since changed quite a bit and adapted into a style staple.
Again, it does have an open lacing system which makes it much more casual.
I think they look best with a pair of gray trousers with the odd jacket – they definitely look great with jeans.
You’re also going to see the Chelsea boots.
These look really good with everything I just mentioned.
Additionally, because they’re going to be simpler in design, they actually sometimes can be worn with a suit.
Now, I know many of you guys are saying, Antonio, I can’t believe you’re recommending wearing boots with a suit.
However, if you live in New York City or you live in Chicago – basically an area in which you get some bad weather, you understand what I’m talking about.
You want to wear boots whenever the weather is not cooperating with you.
Maybe you’re getting a bit of rain or some snow – but you still need to wear a dress shoe and you want something that’s going to go up a little bit higher on the sides, to protect your ankles and socks.
This is the perfect time to take out your dress boots.
5. Try different styles of each
All right, so you’re wondering what is the fifth men's dress shoe that I’m going to recommend.
Guys, I want you to go back and look at the four that I already mentioned.
Find out which one you’re wearing most often and re-purchase them – in a slightly different style or a different color.
So, without repeating myself, each one of these has different characteristics, not just in color but in small variations and sizes.
So, as you're going through them, take look at the different styles of brogues, wingtips, leather finishes.
You can always consider a suede finish when going for something more casual or your standard leather shoes for something more formal but also interchangeable.
Remember, it's always better to be overdressed than underdressed.
Summary – The 5 Men's Dress Shoes Every Guy Needs
Gentlemen, when it comes down to it, you've got to find the right shoe for your need.
In general, I like to go simple – I like to go in darker colors and I like to stay within one color for most of my shoes.
For me, it’s going to be Oxblood and dark brown.
I find that those match most of what I have in my wardrobe – I can dress them up, I can dress them down.
However, some of you guys are going to love the color black and if that’s your case, then make sure that all of your shoes work with each other.
The reason is that, as you're buying these dress shoes, you’re building up an interchangeable wardrobe.
Read next: 10 essential men's shoes to own.
Gents, additional info about dress shoes can be found in my free e-book. You can grab it here.