Your First Dress Shoes - When Sneakers Aren’t Enough

Hello, friends.

Last time, we discussed the first proper suit that every man should own, as well as the pitfalls that we should avoid. Now, what goes better with a fantastic suit than a beautiful pair of shoes?

One thing I can tell you about shoes is that they are addicting. Once you have bought and experienced your first great pair of shoes, you just want more and more and more. There’s a vast variety of different, fantastic shoemakers out there, all offering their own takes and styles on dress shoes. Fine footwear has had an explosion in recent years, with new brands popping up every day, which is beneficial to us as consumers, as that gives us an ever-expanding variety to choose from.

I love sneakers as much as the next guy, but there are many situations in which you can’t wear them. It would look downright odd and would be seen as inappropriate if you showed up to a wedding or interview in a pair of sneakers (unless you’re interviewing for a role in a company that is extremely casual). There’s also a unique feeling that you experience when you wear a great pair of dress shoes, which is difficult to explain, but trust me, once you’ve experienced it, you’ll know what I’m speaking about. It’s a feeling that I never experience when I’m wearing sneakers, no matter how expensive or “cool” they are (Common Projects - I’m looking at you).

I’m not telling you that you need to own dozens of dress shoes in every variety under the sun as I do (once you experience your first great pair though, beware. You may just wake up one morning with a closet full of excellent shoes, for which I take no blame). However, even if you never wear them during your everyday activities, every man should own at least one pair of quality leather dress shoes, and that one pair should be black oxfords.

Black, cap toe oxford shoes

Now, what is an oxford? To put it simply, an oxford is any formal shoe with closed lacing (not open lacing, which was a mistake famously made by Colin Firth’s character, Harry Hart, in the movie, Kingsman: The Secret Service). The lacing style is important, because it is the distinguishing factor between oxfords and derbies (we will have an in-depth article about all the differences between oxfords and derbies, as well as their history, in a later article). The picture above demonstrates the lacing style quite nicely, where the tongue and the quarters of the shoe (where the laces are) are beneath the vamp, which is the area right below the laces and above the toe. This is a lot of terminology to absorb, but I’ll provide another visual to make it clearer.

Black derby shoes

If you compare the shoes in the two pictures above, it should quickly become apparent to you what I mean by closed versus open lacing. If not, well, then feel free to send me pictures of all the shoes you see when you’re shopping, and I’ll let you know.

The oxford has a rich and storied history, and they have been popular as far back as the late 1800s. Black oxfords are among some of the most formal shoes you can own and will be appropriate for around 99% of occasions that you will frequent today. Derbies, on the other hand, are less formal, due to their open lacing. Traditionally, men would never wear black derbies, as they saw it as a formality clash between the black color, which is more formal, and the lacing system, which is more casual. Nowadays, most men can’t tell the difference, but a pair of oxfords is still more appropriate for formal occasion than derbies.

Within the category of black oxford shoes, there are many different types. The most common type you will see today is the cap toe oxford, as seen in the first picture. Another type of oxford is the wholecut oxford, which is made from one piece of leather, without any cap toe or visible seams, as pictured below. The wholecut creates a seamless and extremely clean silhouette, although they can also be seen as more fashion-forward.

Wholecut black oxford shoes

The wholecut is more formal than the cap toe, but unless you frequent black tie events, there is no real reason to choose them over the cap toes. It mostly comes down to personal preference.

You can also find black oxfords with broguing, which are small perforations you see on the shoe.

Semi brogue black oxford shoe

While the broguing does create some visual interest, it also makes the shoe more casual, which is why I would skip it for my first pair of oxfords and choose the cap toes or wholecuts instead. If you’re buying a second or third pair, there is certainly nothing wrong with semi- or quarter-brogues.

Another crucial detail that you shouldn’t overlook is the shape of the shoe, also known as the last. All of the oxfords pictured here have classically inspired lasts, which are more elongated and have a classic round toe. In the 80s and 90s, there was a trend of square toed shoes, which look very dated today, and even in their heyday looked quite ugly and clunky. The picture below aptly demonstrates why you should avoid square toed shoes like the plague.

Square toe black derbies

Yeah… not a very good look. (Also, don’t go typing furiously that these are derbies and not oxfords, I’m well aware of that fact. Just picture in your mind what these shoes would look like as oxfords, and you’ll come to the conclusion that they’re still hideous.) Let’s just leave the square toe to die in the 90s and go with either a classic round toe or chiseled toe on our shoes instead.

In terms of where to buy your shoes from, there are dozens of options, and the only real constraint is your budget. Once again, I highly advise you to skip the large department stores and shoe brands like Aldo and Florsheim. The shoes you find there often use subpar leather and almost always use a cemented construction. Suffice it to say - like the fused interlining we discussed in the suit article - cemented construction is the cheapest construction method available and the shoes will fall apart very quickly.

A fantastic option for just around $200 is Meermin. Yes, $200 might seem like a lot of money for shoes, but these shoes offer a tremendous value, and at their price range, they’re unparalleled. For the price, not only are you receiving a high-quality boxcalf leather from France and a full grain leather lining, but they are also constructed using the goodyear welt, which is much longer lasting than a cemented construction and can be easily be resoled. With those cheap department store shoes, you can pay $100, but you’ll have to replace them every year or so, and the experience when you’re wearing them will be subpar. With a shoe from Meermin, you can easily wear them for years with proper care, and they will only get more comfortable as time goes on.

Another great option at around the $300 mark is Ace Marks. These shoes have all the same great qualities as the Meermin shoes, but they are constructed in Italy and have more of the Italian flair and style. They are also constructed with the Blake stitch method, and although it’s slightly less durable than a goodyear welt, it’s more flexible and can be resoled as well. (Rest assured, there will be an extensive article about the different types of shoe construction.)

There are many other fantastic shoe makers in this price range, which ensures that everyone can find something that suits their style without breaking the bank. If you have a question about a specific brand and whether it’s worth it or not, feel free to reach out and ask!

As to how you can combine your black oxfords, there are several ways to go about it. The most classic option is to go with a suit, in a charcoal or navy (see, I told you I would find a way to tie it in!), for a formal look, or you can go with a blazer and odd trouser combination if you want to dress them down a bit. I would avoid wearing black oxfords with jeans though, as it’s too much of a formality clash and will look odd.

Well, there you have it. Now that are equipped with the proper shoes and suit, there’s nothing that can stop you! Well, not quite, but you will look amazing when you attend your next formal event. As always, if you have any questions or concerns, or if you want to know if this matches with that, please ask in the comments below. Also, if you want me to discuss a certain style topic or item, please leave your suggestions. Your participation and interaction are always highly encouraged, and I appreciate it deeply as well.

Farewell for now!