The Proper Men's Dress Shoe

Sunday, September 25, 2011

The Different Styles
When considering the different types of dress shoes out there, there are a few key elements that separate one from the other. First among them is the question of laces v. no laces. Let's look at a few options:

The first is a black oxford with laces; the second is a loafer (loafers don't have laces); the third is a monk style shoe (with straps and buckles). While there are a few minor differences in the level of formality between these styles, generally speaking, all three will do for most any occasion where dress shoes would be appropriate. Go with the look that you like best.

The next aspect to consider is the toe of the shoe. With the toe there are three things to consider: length, shape, and stitching. Length is pretty self-explanatory (long, medium, or regular). Shapes are generally pointed, round, or square. Stitching can be plain (no stitching), capped, wingtip, apron, or some other pattern (they vary greatly). Here are a few combinations of these elements:

(clockwise from top left)
The first is a black plain toe oxford that is a little bit on the long side. Classic.
The second is a white split-apron toe oxford of medium length. Stylish.
The third is a grey oxford wingtip of normal length. Hip.
The fourth is a brown capped toe oxford of medium length. Dapper.

As you can see, leather colors and finishes are also something to consider. That being said, a classic black or brown is never a bad bid.

The Right Shoe for you
The most important factor to consider while choosing a dress shoe is if you like the look. Even if it is something that you're normally not into, or if it is a little bold for you, I vote that you give it a try. One of my most favorite pairs of shoes that I own has a similar story: I saw it in the store and thought that it was a very attractive shoe, but I didn't really have anything like that; it was not really my style. However, after a little coaxing from my brother, I gave in and bought it. The next day I was clicking my heels because I was so pleased with the shoes.
Beyond liking the look of them, there is another thing that I would consider: profile. If you tend to wear wider or looser-fitting clothing, I would maybe steer clear of the narrow and pointier shoes. Conversely, if you wear slimmer, more fitted clothing, steer clear of the slightly bulkier dress shoes. By matching the wider profile shoe with the wider profile trousers or jeans, you maintain a more continuous line and look from your pants down through your shoes. Although it is a small thing, it helps all of the clothes that you are wearing look like they belong together.
The other thing I ought to mention here is finding a shoe that works for how and where you wear them. Some men wear dress shoes regularly to work or to that interview for where they'd like to work; some to church; some only to weddings and dinners. All of these are normal places to wear them. But every once and a while, if you don't have this practice, I invite you to wear them with some nice jeans and a nice collared shirt or tee; this can bring some competent class to your everyday look. Whatever the occasion, when you need to look your best, a proper dress shoe is not only a "nice touch," but a necessity if you want others to recognize your competence and sense of propriety.

Finding the shoes
The last thing to consider is where to find the shoe. I generally start by looking either in a shoe store or on a site that has lots of different types of shoes (e.g. From there, I find elements of shoes that I like or a brand that seems to fit your style, then focus on that. Although buying shoes online can be a little scary for some people, most proper online merchants have an excellent return policy.
My other favorite way is by going to outlet stores and places like Ross or TJ Maxx. The reduced prices are what it's all about. I refuse to pay full price for any article of clothing. Browse clearance racks and discounted stores, and, with time, you just might find a treasure. I once found some great $130 Guess loafers for $15 at Ross; jut my size. Even if you're not necessarily looking to buy, take a look around and figure out what styles interest you.

Conclusion: Dress shoes make you look good. Don't be afraid of a new style. The possibilities are practically endless, so if you take a little time, you'll find something that you can be proud of wearing.


(images in this post from,, and


  1. This post's timing and content is serendipitous because yesterday I started university classes again and I decided to wear a black shirt, jeans and black leather dress shoes. Though slightly worried that I might be committing a faux pas, or coming off as pretentious, in fact when I was there I was pleased with my decision to slip the surly bonds of hoodies and trainers. One question though - Why Victoria station with a picture that is clearly of Gallic origin?

  2. But yes- I meant to say - your post comes as timely confirmation of my choice.

  3. Mark,
    Happy to hear that your decision worked out for you. I'll still do trainers and jeans all the time, but a pair of dress shoes with jeans makes me feel like a million bucks (or £639K).
    As far as the photo of Gallic origin paired with Victoria station is concerned: the photo illustrated some of the feel that we're going for in this blog; the name will stay the same, but the photos will change from time to time. Next time I'm in Victoria station, I'll be sure to snap a sharp shot for the blog.

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