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The First 5 Dress Shoes Every Man Should Buy & In What Order | Upgrading Your Shoe Collection

What are the most expensive shoes that you own? Let me know down in the comments. I will like to hear from you guys. Now, believe it or not, I bet I can guess the most expensive shoes in your closet. How can I know this? Because, guys, it’s easy. The most expensive shoes you own are the ones that you never wear. Make sense? If you go out there and you buy a $100 pair of shoes and you wear them once. You go out there and you buy $350 pair of shoes and you wear them 350 times, guess what? $100 per wear, a $1 per wear, which one was the better deal? Gentlemen, shoes are one of those items that you want to get right because good shoes are expensive, however, if you get the right pair in the right order, you’re going to get your money’s worth out of them especially if you take care of them. In today’s article, I’ve got five pairs of shoes I’m going to recommend to you guys and the order to purchase them. We’re talking about dress shoes here. You can also check out our collection here. You will be glad you did. There aren’t an exact right five pairs of shoes. However, I want to get you thinking about that. When you start to think about this and you pay a little bit more attention, you’re going to make sure you make your own smart purchasing decision. All right? Let’s get into the first pair of shoes that you want to own. We’re talking about balmoral oxford, something that has closed lacing.

Now, this is a wholecut dress shoe. I put it here because guess what? It’s pretty much got the elegance simple look, but here it’s going to be a more classic one with the closed lacing system. This one has a cap toe, it’s in a dark oxblood colour. This will work fine for wearing with a suit and that’s what you want your first pair of dress shoes to be able to do. You should be able to wear them with a suit for a wedding, for a funeral. You’re meeting with the president, meeting with the CEO of your company, you’re simply getting dressed up for your little girl’s communion.

This is when you want to look your best and you need to have that pair of shoes that works with it. Now, black is going to be the de facto colour for a lot of you guys. Be careful though even though you’ve got closed lacing on this pair of shoes, we start to see a little bit of broguing here. So, once you start getting into cap toes broguing, all of a sudden the formality of it is going to start to go down, you could still pull this off with a suit though.

Next, let’s go on to Bluchers. So, the second one and the big difference here is going to have an open lacing system, not a closed lacing system, so that’s the key differentiator.

You’ll find that these shoes, in general, are going to have maybe broguing or they’re going to have ornamental stitching, they’re going to be lighter in colour oftentimes. So, these are going to be your more casual dress shoes. These you can still sometimes pull off with a suit, but they’re going to look better with occasionally dark-coloured jeans at the probably the most casual. And then, but you can always dress them up with a pair of, you know, grey flannel trousers, just regular dress slacks maybe with a sports jacket. These are going to be very versatile. These are great and I think should be the second pair of shoes in a man’s wardrobe.

Next, let’s go to the slip-on. So, I’m going to have a wide variety of slip-on I’m going to show you.

The reason I love slip-on is that they’re casual, they’re comfortable. Guys, when you are traveling you’re going to the airport very easy to take on and off to be able to go through that metal detector. They come with a wide range and most men don’t think, I mean the monk strap. Not technically a loafer, but I’m going to lump into the slip-on because you don’t have to lace anything up. And I love, I mean single, double, it doesn’t matter where you go.

Again, I like to go within general darker shoes and I know I’m not talking about colour a whole lot there.

Tassel loafer is going to be a little bit less formal than the monk strap, but I find many men, especially in Nigeria, pull this off with a sports jacket, odd trousers combination. You can wear it with jeans, it’s going to look great. Occasionally if it’s in a very dark color, maybe a black color, you can actually even pull it off with a suit although you want to be careful in bigger cities.

The fourth shoe style that I’m going to talk about, gentlemen is the dress boot. Chukka is a perfect example of this. So, chukka comes out of the English, I believe it’s the word time desert boot. It has since changed quite a bit. It does have an open lacing system so that right there is going to make it much more casual. I think this looks best with a pair of, you know, grey flannels maybe trousers with an odd jacket with jeans that looks great.  And 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, I can’t believe you’re recommending wearing boots with a suit. However, if you live in New York City, you live in Chicago, you live in an area in which you get some bad weather, you understand what I’m talking about.

Because you want to wear boots whenever the weather is just not really cooperating with you, you’re getting rain, you’re getting some sleet, you’re getting some snow, 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 and protect your ankles and socks.

All right, gents, so you’re wondering what is the fifth dress shoe that I’m going to recommend. Guys, I want you to go back and look at the four that I just mentioned, find out which one you’re wearing most often and repeat it may be in the slightly different style slightly different colour. So, as we’re going through I didn’t really even talk about brogues, wingtips, but these would be a great addition as a fifth shoe.

Gentlemen, when it comes down to it, you got to find the right shoe for your need. In general, though, I like to go simple, I like to go in darker colours and I like to stay within one colour for most of my shoes. For me, it’s going to be oxblood and dark browns. I find that those are going to match most of everything I have in my wardrobe, I can dress them up, I can dress them down. I’m not necessarily a black shoe man, however, some of you guys are going to love the colour black and if that’s your case, then make sure that all of your shoes kind of work there and the reason is that is also and you’re building up your interchangeable wardrobe.

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