4 Dress Shoes Every Man Should Own

It is impossible to be well dressed in cheap shoes . . .worse, the wrong shoes.

Good footwear does add a fabulous amount of style and class to your wardrobe. So it’s important that you familiarize yourself with the shoe guide. There are books written about shoes that could really go into a lot of detail, but this guide is meant to help you generally understand shoe types, the level of dress and what style of shoe can be worn with what style clothing.

There are the four most common dress shoe styles found in a man’s wardrobe that should be on your list. There are at least a dozen styles, but having this basic selection can already complement your basic attire.



A classic shoe style with a formal, elegant and dressy appeal. An Oxford is a lace-up shoe where the eyelet facings are stitched underneath the vamp (front section of the shoe). This style of shoe is sometimes called a closed front. It comes in any color although black and browns are most popular. Every man who owns a suit should own a pair of classic oxfords that are minimally styled.

  • Style variations: plain toe, cap toe, brogue, and whole cut.
  • Special Note: Appropriate for a suit, if casually styled works with sport jackets and odd trousers. Do not combine with jeans or chinos.






The Derby is a very similar to the oxford shoe but the difference is in the lacing where the eyelet facings are stitched on top of the vamp (front section of the shoe). This style of shoe is sometimes called an open front. Less dressy than Oxfords and are less suited for suits but do make a good shoe choice for business attire on rainy days due to their more rugged creation.

  • Style variations: cap toe, wing tip, brogue, wide variation in materials like suede and mixed leathers. Common variations are saddle shoes, derbys, spectators, and laced moccasins
  • Special Note: A well-dressed guy know these can be worn with a suit, but are better with an odd jacket and trousers. Derby can be worn also with jeans assuming they are casually styled.









Loafer’s are the traveling businessman’s best friend. They slip on and off easily when going through security airports, they are comfortable, and versatile.

  • Style variations: monk straps, tassel loafers, penny loafers, unlaced moccasins.
  • Special Note: The sleeker and simpler the design the more formal it is. Also, darker colors are more formal (black being the most formal), and the less of your socks are visible the more formal the look. Loafers look great with jeans and dress pants, as well as with suits when not wearing a necktie.






Dress boots are a sleek and minimalistic boot style that can be worn with jeans, odd trousers, and suits (in rainy days). If wearing under fair weather conditions, boots should be worn under the rules applicable to a pair of informal bluchers.

  • Style variations: cap toe, wing tip, broguei, wide variation in materials especially water resistant leather cuts.
  • Special Note: Only wear with suit in rainy days or if you travel to countries with snowy weather.



Now that you know the most common types of dress shoes, selecting the right colors is the second most important thing you need to know.  We’ll discuss the quality and craftsmanship in the next article. The rule of thumb here is that BROWN goes with everything and your safest bet when choosing your shoes with any outfit you’ve put together, except for a black outfit – only BLACK shoes goes with that. When you’re dressed formally, brown shoes complement well without drawing attention away from everything else you are wearing. If you’re dressed casually, selecting dress shoes that are brown will make your casual get up look more sophisticated. Simply put, brown has great crossover quality and something to consider when you’re selecting your dress shoes.

So, go crazy with the different shades of brown when selecting your next pair of dress shoes that will last you years and complement most of your outfits. . . just don’t forget a few pairs of black for your black suits.



By Justine Castellon

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