Shoe Basics

It may surprise you to know that there are just as many types of shoes and boots out there for men as there are for women. Take a breath with me as I name just a few. Aaaand oxfords, derbies, loafers, monk straps, bluchers, wingtips, spectators, full brogues, semi brogues, quarter brogues, longwing, patent leather, whole cut, opera pumps, jodhpurs, chelsea, chukka, boat, kilties, and the list could go on still. Everything I just named above is either a category of footwear or a specific detailing that can help differentiate a piece of footwear.

If all that seems a bit overwhelming- I have good news: in today’s article we will just be focusing on the most commonly worn formal shoes for men. By no coincidence, they are the first four that I mentioned.

Oxford

Brown cap toe oxford shoes from Joseph Cheaney and Sons.

An oxford shoe is categorized by its closed lacing system. The shoelace eyelet tabs are attached under the vamp, also known as the “upper” since it is the part of the shoe that covers the top of your foot. Oxfords can come in many different forms, but many of them contain a horizontal stitching running just under the lowest lacing eyelet (see picture above). This an easy way to tell if a shoe is an oxford.

Oxfords are the definitive men’s formal shoe. As a general rule of thumb, 2 factors decide how formal a shoe is:
– Color; the darker the shoe the more formal it is
– Decorum; the more “blank” a shoe is the more formal it becomes. More stitching or brogueing makes a shoe more casual

Oxfords have earned their place at the top of the formality food chain due to their elegant nature. They are worn for black and white tie events, working in the office, weddings, funerals, religious practice, interviews, or perhaps a date you decide you’d like to dress up for. Oxfords tell the world that you mean business, and you’re here to be taken seriously.

Derby

Derby shoes from Undandy.

Derbies, also known as bluchers, are characterized by an open lacing system where the shoelace eyelets are attached on top of the vamp. Derbies are a rung below oxfords on the ladder of formality. They are not to be worn to black or white tie events even if they are dark with minimal decor. Otherwise, they’re perfectly suitable to wear to the office or other fanciful events.

Depending on the size or shape of your foot you may even prefer derbies. The extra pieces of leather sewn onto the vamp allow for more adjustment, making derbies easier than oxfords to slide onto your foot before you tie them, and adjust the tightness later if necessary. This may be especially advantageous to you if your feet are prone to swelling.

Left: a derby with open lacing
Right: an oxford with closed lacing

Loafer

Penny loafers from Cole Haan.

Loafers are a moccasin type shoe that lack any sort of fastening system. In your household you might even call them “slip ons.” These shoes rank below both oxfords and derbies on the formality scale, but are still quite versatile shoes because of their more casual nature.

Loafers look quite natural with casual suits, business casual attire, khakis, chinos, and even denim. Black loafers could be used to dress down a formal suit, or different shades of brown loafers to dress up a pair of nice jeans and a button up shirt. If you already own a pair of oxfords and derbies, consider loafers to be your next shoe purchase.

Monk Strap

Brown monk straps from Francesco Benigno.

Christian monks in Europe during the Middle Ages commonly wore a work shoe or boot that utilized straps and buckles for their fastening system, hence the name of these shoes. Monk straps will typically be found with one or two straps but there are some styles that sport three straps on each shoe.

There is some debate on where exactly monk straps fall on the formality scale. Some put them between oxfords and derbies, while others consider them less formal than derbies. Whichever is the case, monk straps can certainly be worn with anything and just about anywhere you can wear derbies.

Among the general populace, these shoes are the least commonly worn of the 4 I have written about today. The buckles make monk straps a bit flashier than the others and so may require a bit more confidence in order to wear, but they are an excellent addition to your collection if you already own multiple pairs of formal shoes.

Recommendations:

  • if you only require one good pair of shoes for dressing up now and then, buy a pair of black cap toe oxfords.
  • many brands refer to any formal shoe as “oxfords” even if they are derbies. Shoes from these brands are typically of lower quality
  • be sure to select loafers that will fit your feet as closely as possible after they are broken in- there is no way to adjust them organically
  • select monk straps with 1 or 2 straps. 3 straps is excessive and looks cartoonish, and will almost certainly draw attention to your feet