Men’s Leather Dress Shoe Styles

Understanding Men’s Dress Shoes isn’t difficult.

Like most things in life, if you break it up into sections and apply a few guidelines it turns out to be pretty simple.

This guide is a overview of mens dress shoe formality meant to help you “generally” understand shoe types, the levels of dress, and what style shoe can be worn with what style clothing.

Note – this chart does make generalizations that some shoe afficionados may have issue with. I admit it’s not perfect – if you have suggestions, email me.  In later articles we’ll tackle the issue of color matching and address specific styles like suede and cordovan.

mens dress shoes

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Balmoral (Bal)

  • The dressiest oxford men’s footwear selection. Sleek, refined, most often sold in black or brown but appropriate in any dark conservative color.
  • Style variations include plain toe, cap toe, brogue, and whole cut.
  • Appropriate for a suit, if casually styled works with sport jackets and odd trousers. Do not combine with jeans or chinos.
  • Every man who owns a suit should own a pair of classic oxfords that are minimally styled. If you wear suits daily you should rotate three pairs or more.
churchs diplomat mens classic oxford

Church’s Classic Oxford – Diplomat

Men’s Bluchers

  • Less dressy than Bal oxfords, identified by lacing system sewn outside of shoe.
  • Well dressed men know these can be worn with a suit, but are better with an odd jacket and trousers. Can be worn with jeansassuming they are casually styled
  • Style variations include cap toe, wing tip, brogue, wide variation in materials like suede and mixed leathers.
  • Common variations are saddle shoes, derbys, spectators, and laced moccasins
  • A classic shoe that should serve as your 2nd or 3rd pair depending on needs -the more extreme the styling, the less versatile the shoe.
mens classic black brogues

Black Bluchers

Men’s Dress Boots

  • Dress boots are meant to be worn when the weather dictates protecting the ankles from water, mud, and snow -in levels of formality they should not be worn with a suit, although they can if the weather calls for it. If wearing under fair weather conditions, boots should be worn under the rules applicableto a pair of informal bluchers.
  • Style variations include cap toe, wing tip, broguei, wide variation in materials especially water resistant leather cuts.
  • Appropriate for a sport jacket and odd trousers or jeans. Only wear with suit in rainy/snowy weather.
  • A man should consider boots if he is exposed to conditions that warrant their wear -otherwise, reserve them for your 4th to 5thpair.
mens monk strap dress boots

Monk Strap Dress Boot

Men’s Loafers or Slip-ons

  • The least dressy choice, they are a product of comfort and convenience.
  • Only with a suit when traveling, they are at home with a casual odd jacket and trousers minus necktie. Can be worn with jeans or chinos as well.
  • Style variations are wide -usually the more delicate and closer resemblance to oxfords the more dressy. Also, the greater the exposure of sock the less formal.
  • Common variations are monk straps, tassel loafers, penny loafers, unlaced moccasins.
  • Loafers are a travelers best friend -easy to slip on and off when going through airport security or when relaxing on the plane,I recommend they be the 2nd pair a traveling man owns or the 3rd pair for a man who like to look sharp around town in jeans and button down shirt.
mens classy slip-on loafers

Men’s Dress Slip-on Loafer

Images courtesy of Leffot Men’s Dress Shoes – Visit their blog for an amazing collection of images and information.

RAW Transcript


Hi. This is Antonio over at “Real Men, Real Style” and I’ll be talking today about demystifying dress shoes in 60 seconds or that’s the title that I decided to give the article and really, the whole point of this is to show that understanding dress shoes is not difficult so I’m going to mix reading this article and to kind of giving you a little bit of a deeper understanding as to where I was going with it and the points I was trying to make.

Understanding men’s dress shoes isn’t difficult. Like most things in life, if you break it up into sections and apply a few guidelines to it, it turns out to be pretty simple. This guide is an overview of men’s dress shoe formality meant to help you generally understand shoe types, the level of dress and what style of shoe can be worn with what style clothing. Now this is an important point. I put a note here but this is a simplified version. There have been books written about shoes and we could really go into a lot of detail here but this guide is for the young man or for the gentleman who just doesn’t know a whole lot about shoes and is looking for clarification literally in 60 seconds.

Let’s say he’s at a shoe store and he needs to pick up a pair of shoes for a wedding that weekend or he just wants, it’s not something that really interest him but he wants to understand why is it that people frown on him when he wears loafers with a suit or why do even boots exist in dress wear. I mean, typically when men think of boots, you think of something that’s more, I would say, more utilitarian in a sense of boots as American’s we think they should be work and dress boots, they are a bit rougher but there still dress. Their in the category of dress shoes and I keep them there. So as you’re listening to this, you can actually see the chart but if you go to the website, and then go to the article, “Demystifying dress shoes.” It’s going to be under Men’s Style Basics or Clothing, right under shoes so you should be able to find it and you can download it. It’s a pretty big chart. I’d say it’s around 1400 pixels across, 800 pixels high which is basically, it’s bigger than a, about twice the size of 2 sheets of paper and the reason we made it big is so you can print it off, you could put it some place. I see a shoe store or maybe even somebody at a small company, kind of putting this out so that men can pick up.

We break it into 4 sections. Now as I wanted to note before, this isn’t the normal 4 sections that you would break shoes into. It’s 4 sections that we came up with because technically there are both balmorals and bluchers, those both fall under the same category which is Oxford shoes, any shoe that’s got a lace up and boots are probably actually, there’s multiple categories of boots and the boots that we show in the picture are slip on. Also I apologize if I mispronounce things. I’m a product of the Texas public education system and I did not actually grow up wearing a lot of this stuff. I’m a self taught men’s style expert so a lot of the way I’m pronouncing things are simply the way I read them.

So the first, getting back to the chart, break it up into 4 parts. The 4 parts starting at the top are the most formal going out the bottom are the least formal however you still can wear, I mean we’re talking about dress shoes so sneakers aren’t in here and you don’t have to worry about any of that kind of stuff confusing things. So let’s talk about Balmoral. Okay so these are what’s commonly known as Oxfords but Oxfords do include the second category which are bluchers so for right now I’m going to just call them Bals. Now these are the dressiest Oxford men’s footwear selection you can go with and the big thing about these is it the lacing is closed. If you look at, basically you’ve got a very smooth looking shoe. You don’t have, it doesn’t look like leather has been strapped on to the side and sewn on to the outside. That is the big thing and it’s something that you, it would help if you came and you looked at the image because I try to show, once you see it, you’ll know it but Bals are usually sleek.

They’re refined. They usually come in dark colors with, I would say, non, they do have a few style variations but they’re usually very simple. You’ll see just a plain toe, occasionally a little bit of brogue, sometimes you’ll see a whole cut which is about a smooth of a in sleek of a leather shoes you can get. Imagine, it’s cut from just 1 piece of leather the entire top of the shoe and so Bals basically Oxfords are perfect for suits and this is what they’re really made for and in fact you can wear a pair of these if their black and if their shined properly with a tuxedo but every man, I would say, this is the first dress shoe that a man should have. And something like I think of a cap toe, Oxford is perfect and that’s something you’re going to get a lot of miles out of. You’re going to be able to wear it with a suit. You’re going to be able to wear it with a sport jacket and odd trousers. When I say odd trousers, I just mean slacks that don’t have a jacket that goes with them so you can wear it with grey flants. It’s going to be too dressy though. For Chinos or for jeans and so again this is something that, these are your dress up shoes and you want to, every man should have one pair. Every man should have a suit and every man should have a pair of classic Oxfords.

Okay, now moving on to bluchers. These are less dressy simply because they have, if you look at them, it looks like the leather has bit because it has, has been attached to the outside of the shoe and this is actually right where the lacing system’s at. They were developed, the general’s name, I’ll bring that up with another one but basically they’ve been around for a couple of hundred years and they can be worn with a suit if the shoes are very conservative but they are a little bit less formal of a shoe and they’re more at home to be worn, I would say, with a sports jacket and a pair of odd trousers and this is where you’re going to see a lot of style variations. Most of your suede shoes, your wing tips, shoes that have a lot of brogue design. When I say brogue, I mean, basically cutting and designing in the leather. You’re going to see a lot of that with these so these are the type of shoes that you’re going to see just a lot of men. You have a lot of flexibility with these and because of that, they are less dressy and always remember, the more extreme the styling, in a sense, the less versatile the shoe because people remember that. So let’s say you got a purple pair of, purple suede of bluchers. Now that’s a great, it’s a classic shoe. It’s something that you can wear and it will look great but you’ve got to understand that you can’t wear those very often because otherwise you’re going to be known as the guy with the purple shoes. So you’re going to, I would recommend that for a second or third shoe, a man go with the blucher but he go with something that is pretty conservative. So if you’re classic Oxfords are black, go with your bluchers, go with those being a dark brown or something like that and go with a very simple design.

Again, your first group of shoes, you want to keep those very simple so that you can get the most miles out of those and examples of this are saddle shoes fall in here, spectators, lace moccasins. So under this we have boots but this is a bit deceptive because boots actually can be a bit dressier or they can be less dressy. Boots kind of fall all over the place but the reason I put boots here is because boots come into the play when the weather calls for them and if it’s rainy outside, if it’s snowy, you want to wear boots because they protect the ankle, they usually got a sole which is a bit tougher although not always. A lot of the Chelsea dress boot usually has a leather sole that’s not really any stronger than what you would find on Oxfords but boots because of their design, I mean I live here in Wisconsin. And right we’ve got probably 10 inches of snow out there. If I’m going out, I would rather wear boots than a regular pair of dress shoes even if it’s a really dressy event, simply because snow is not going to get into, snow would get into my socks if I was wearing regular dress shoes. As I go out, well not so much, I would go through my garage but…

…whenever I’m outside, you can just imagine. You don’t want to get snow in your socks so boots, again, they cover the ankle. They do have that added bit of protection and their more of something that you want to own a pair of dress boots if you’re in an area, let’s say Seattle, Washington or if you’re over up in Maine or somewhere in New England where you’re walking around a bit outside, you’re going to be exposed to water. Now you do need to take care of them just because they are boots, does not mean you don’t need to waterproof these, you don’t need to clean them after wearing. They’re simply going to do a better job of covering and did I miss anything on boots? I think they should be really a man’s 4th or 5th pair and I lean towards 5th pair unless you are in a area that really calls for them because of the weather.

The last thing we talked about or the last shoe I talked about are loafers and slip ons. Now these are the least dressy and simply because they slip on, they’re closer to the slipper. There something a man would wear around the house but there is an exception and that is if you travel a lot. I would say simply because of their convenience, the comfort and the ability to simply take them off and to go through security screening. To me, makes the loafer slip on a must, possibly second shoe that a man should own if he travels and if he travels quite a bit, he should own a few pairs of loafers and they come in a wide variety. You can have some that do a good job covering up most of the foot and have a very sleek shape and are very dressy and to most people, they would not even notice. You could wear these for the suit and they wouldn’t even notice that you’re actually wearing a slip on. And then they are a much more casual moccasin style ones which by the material and by the more square design are very, very casual shoes and these are going to be at home more with jeans or chinos. Let me see what else. Did I miss any points?

I kind of alluded to this but the more of your socks that you expose with the slip on, the less formal that slip on is. The only exception is the upper pump and that’s what you wear with the tuxedo and that traditionally goes with it. Common variations are monk strap, tassel loafers, penny loafers, unlaced moccasins. I love them on the strap. If you haven’t seen it, it’s one of my favorite shoes and it’s not as common in the United States and it’s something that draws a little bit of attention and so it is a little bit less casual. It shouldn’t probably be worn with a full on suit but I think for a sport jacket, a blazer and grey flamel trousers, it looks sharp but what you got to pay attention to with the monk strap is you’re introducing metal so you got to make sure that you’re metals match. If you’ve got a pair of monk straps and they’ve got a silver buckle, you’ve got to wear actually a belt with a silver buckle if you’re wearing a belt and you try to match it also with your watch. Wedding rings, that doesn’t matter. You don’t have to match those.

And that would be it for this part. We do have some really good links on the article. I like over to a There’s a great overview of men’s dress shoes there and I also give a big thanks to Leffot. They’re a men’s shoe store in New York City and I took a lot of my photos, actually most of the photos from their website and they sell all of the shoes here that you see on the website, an amazing company, just give Steven a call. He can do mail orders and highly recommend them. Alright, that is it. This is Antonio with “Real Men, Real Style” and I hope you enjoyed this little podcast. Have a great day. It’s evening here but take care and we’ll talk to you soon.

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