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.
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.