Dress Shoes for the Boss!

A good pair of high quality leather shoes will give any person the confidence their shoes are “boss” because as the saying goes “Like white shirts, delicate watches and coattails, the very lack of practicality is what makes them dressy.”

In General, You Must Consider these Main Factors With Dress Shoes:

  1. The shoes are made of quality leather (e.g. calf, veal, full grain leather, and etc.)
  2. Soles should be made of leather not rubber. (leather soles has its pros and cons but they are considered classy and superior to rubber soles)
  3. The soles are stitched to the shoe instead of glued.
  4. The stitching should be neat and quite subtle.
  5. The lining of the shoe, should be made of real and not synthetic leather.

Here is an image of my favorite go to shoe! I recommend this because it is classic and simple.


The shoe above is a Magnanni Luca Oxford shoe that is made by a highly skilled craftsmen. I wonder if they named it after Luca Brasi from the Godfather!

Notice the stitched soles on this dress shoe. Stitched soles are always better than glued soles because they make the shoe more durable to wear and tear!



Some people argue that rubber soles are more practical than leather soles and this is true to a certain extent. From a safety standpoint,  rubber soles have more traction and work well in the rain and hazardous or slippery areas. Leather soles look better for most but have less traction that can cause hazards! one advantage with leather soles is that the sole molds to your feet making the shoe become more and more comfortable after each and every wear.

Here is another of favorite I use to alternate between my Johnston and Murphys! It’s called the Magnanni Santiago Oxford! This shoe is a personal favorite of mine! It’s rich brown color comes with a sophisticated sense of style.



From an economic standpoint, it would be wise to buy a quality pair of dress shoes to save money. Many of those who skimp out on the quality of shoes pay the price of having to buy more shoes within a short time frame. Therefore, it can be safe to conclude that it is better to have a good pair of quality shoes that can last several years than having to buy pairs almost every year.


~ Captain Vimes ‘Boots’ Theory of socioeconomic unfairness.

The next criteria in choosing a dress shoe is the style.

For business and formal wear, simple is always best. An oxford or a cap-toe oxford (seen below) is probably the best kind of business shoe out there. Do you know the difference between and Oxford and a Derby?


These are oxfords.


This is a derby.

The pair of shoes above has closed lacing while the shoe below has open lacing.

Here is an image to clarify!


Those with closed lacing are Oxfords while those that are open are derby type of shoes. Oxfords are more formal but derby shoes are more flexible and comfortable. This is why military dress shoes are derby types. Same goes to the type of shoes FBI special agents wear for work.


If it’s your first pair, simply get black. The color black is the most versatile color that can compliment almost any color of suit you can wear.

Then to add a little flavor to your style, try to opt for dark brown or burgundy. I find that dark brown shoes add a bit of sophistication to the wearer and the color brown highly compliments grey, charcoal, and navy suits. Just don’t wear brown shoes with a black suit.