How to find the best shoes and belt to match your outfit

Hey fellas! This blog marks the halfway point in our year of exploring essential wardrobe basics. I hope you feel like you are starting to get a grasp on how to build a wardrobe that suits you and looks good at the same time.

Today, we are shifting our focus down — to belts and shoes. Let me start by saying that we are surrounded by about a million and one different types of shoes and we will not have time to cover everything today. But we will cover a few basic types that I think are important for the modern professional gentleman.

Let me start by talking about the basic construction of the modern men’s dress shoe. The shoe is made up of four main components: the toe, the vamp, the facing and the quarter. The toe is the very front section of the shoe. The vamp is the mid-section of the shoe, between the laces and the toe on the shoe. The facing is the section on top where the laces sit (if the shoe has laces). The quarter is the very back section of the shoe that holds the heel. Variations in these four sections are the defining factors in what makes styles of shoes different.

Here are the main styles of shoe that the modern gentleman needs to know.

  • The Oxford — This style of shoe gained popularity in the 1800s and is characterized by its low top and closed lacing, meaning the facing is secured under the vamp. This type of shoe is a classic and can be paired with pretty much any outfit.
  • The Derby — Similar to the Oxford, but a bit more casual, this shoe gained popularity in the 1850s. The main difference between this style and an Oxford is that it has open facing, meaning the quarters are sewn on top of the vamp. This makes for a bit more flexible fit and a slightly more casual shoe.
  • The Monk Strap — A Monk Strap has no laces and has a casual level that sits between a Derby and an Oxford. It gets its name from its origins — this shoe was originally worn by the monks as a close-toe alternative to their classic sandals. This style is quite eye-catching and adds a lot flair to an outfit.
  • The Loafer — This shoe is a moccasin-inspired slip-on shoe. Originally designed as a slipper for King George VI, this style became publicly popular in the U.S. in the 1930s. Its defining characteristic is an elevated seam running along the toe of the shoe. A Loafer can be worn with a suit or with a more casual look.
  • The Dress Boot — This guy is best explained as an Oxford or Derby shoe (depending on its structure) with a longer shaft. This style originated in the Victorian era and can be worn formally, as long as the boot features a dressy heel and thinner laces.
  • The Chelsea Boot — This shoe is a laceless ankle boot originally designed as a practical option for equestrians in the Victorian era. Today it is a classic, more casual option for any stylish guy who wants to look good without working hard. It is identified by its round toe, low heel, and elastic gussets. You probably wouldn’t wear this style with a suit, but it can be worn with anything in the casual to semi-casual range.

Those are the main types of dress shoes we are going to cover today and you can pick and choose which ones you need and want based on your lifestyle, However, I have done this long enough to know that some of you want me to tell you exactly what to get. If I must, here are the five pairs of shoes you should definitely own: Black Oxfords, Brown Oxfords, Brown Derbys, Brown Loafers and Chelsea Boots (in either black or brown).

OK, now that we have covered shoes, let’s discuss belts. The good news about belts is there isn’t a ton you need to know to look good. First, make sure your belt is between one and one and a half inches. Anything wider might have you looking a bit clownish.

Most of you probably know the color of your belt should match the color of your shoes, but the advanced tip I will give you today is this: Make sure the metal on your belt matches the metal of any other accessory you are wearing.

While there are many materials of belts to choose from, I absolutely recommend that you start with leather belts. Leather will always be classy and looks good with multiple different style levels. When deciding what belts to invest in, I would first buy a black leather belt and a brown leather belt that matches the majority of metals you wear.


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