Gentleman’s Shoes – The Oxford, The Derby, The Brogue, and the Monk Strap…What They Are and Why You Should Know the Difference.

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Up until relatively recently, I was the sort of man who just had a few pairs of shoes that I had bought without much thought; based on their general look, comfort and, mainly, the price. Whilst loving nice clothes and spending a bit on suits, I usually assigned myself a relatively minimal budget for footwear.

Recently, however, I acquired a copy of ‘Gentleman‘* by Bernhard Roetzel. A mighty tome that has been translated into many different languages. Roetzel is a real authority on how to dress like a gentleman.

I was shocked, then, to read that he deemed good shoes to be the most important element in a gentleman’s wardrobe above all others. Stating that: “if a trainee or student has 600 dollars a year to spend on clothes…he should plan to spend half of it on shoes…”

So I started researching what I had long taken for granted. The more I’ve found out about different shoes, the types available and how they are put together, the more obsessed I’ve become with this, and wanted to share what I’ve learnt.

If you want to spend your money wisely when looking for good shoes, this is what you need to know. In this post I focus specifically on four of the major types of shoes – The Oxford, the Derby, the Brogue and the Monk Strap.

“It would be better to go through life barefoot wearing just socks…than to lose face by wearing cheap shoes.” (Rotezel, 2016, p160)

The Anatomy of a Shoe

If you really want to understand different shoes, it’s important to first understand how they’re put together. Some parts are more obvious than others, but these are some of the less obvious parts:

  • The Vamp – runs across the top of the foot, and is an important element in distinguishing between the two classics of the shoe world – The Oxford and the Derby.
  • The quarter – the section at the side of the shoe, that sits between the heel and the vamp.
  • The upper is, essentially, the whole of the leather part of the shoe (so just excludes the sole)
  • The insole (not pictured) is the inner part of the shoe that the foot rests on.
  • The outsole is the bottom of the shoe that makes contact with the floor.
  • The welt is a piece of (usually) leather, and runs around the perimeter of the shoe, joining the upper to the sole. A good quality shoe seems to be the ones where the welt is stitched down. If you’re interested, I’ve found some good videos about this on Youtube.
  • People often talk about ‘the Goodyear welt’ being particularly good (see below), but be aware that, whilst this strengthens the shoe, it can take a bit longer to break them in.
A Goodyear welted shoe, at Charles Clinkard, Burford Oxfordshire (no affiliation). The stitch runs around the perimeter of the sole.

Okay. So now you know a bit more about how a shoe is put together, lets look at the different types:

The Oxford v The Derby

The two best known types of formal shoe are the Oxford and the Derby. Know the difference and the mystery of all the different types of shoe will become much simpler.

The Oxford

An Oxford has ‘closed lacing’ meaning that when you draw the laces in to tie them, the two sections of leather (usually) touch, so you don’t see much of the tongue. Also, and what gives you this effect, is that the part of the shoe with the eyelets/laces is stitched underneath the vamp giving you a smooth line across the top, across the vamp and the quarter. Due to this sleek look, the oxford is the most formal of shoes.

An Oxford, by Barker at Charles Clinkard, Burford (no affiliation).

The Derby

The Derby has an ‘open lacing’ meaning that you can usually see some of the tongue underneath when they are tied. The most distinguishing feature though is that the eyelets, the part of the leather that holds the laces, is stitched to the outside of the vamp/quarter (see below). The Derby isn’t as formal looking as an Oxford, so is a more diverse addition to your wardrobe.

Trying on a Derby at Leonard Jay, Oxford (no affiliation).

The Brogue

Okay. Here’s another important fact – the brogue is not a type of shoe. It’s the pattern on a shoe. Most Brogues are Oxfords like those pictured below (again, because you get a smooth look) but you can get Derby Brogues too. A wing-tip Brogue has the pattern across the toe raised into a point (see below), whereas a straight brogue has the line across the toe-cap. You can also get Derby Brogue boots.

A nice line of wing-tip, Oxford Brogues from Barker, on display at Leonard Jay in Oxford (no affiliation).

The Monk Strap

The last type of shoe that I want to discuss is something called the Monk Strap. This is, essentially, a shoe without laces, that has a piece of leather attached to the inside quarter, which crosses over and is buckled to the other side of the shoe (see below).

They can have one or two buckles. Again, they are not as formal as an Oxford, and will certainly add some diversity. However, I’ve discussed his with a number of people and get the impression that they’re the Marmite of the shoe world – you either love them or hate them. Personally I love them.

A Monk Strap, from s.Oliver at The Oxford Shirt Company, Burford Oxfordshire.

And there you have it. You should now know some of the different parts that make up a shoe, and the difference between some of the more common, formal types of men’s shoes available. Hopefully this will prove useful when you next need to make that all important purchase, or if you just want to show off a little bit of gentlemanly, shoe-related knowledge.

*please be aware that I’m part of the Amazon UK Affiliate programme, so if you buy anything through some of the links provided, I may get a small percentage at no extra cost to you. This helps towards the blog and I only ever post things that I genuinely recommend.

Thank you to Leonard Jay in Oxford for helping me with some of the research for this post (no affiliation).

Thank you for reading this post I hope you enjoyed it. If so please don’t forget to like, share and subscribe. (:

References & Recommended Reading:

Rotezel, B. (2016) Gentleman * h.f Ullmann Publishing

Cool, S. (2019) How to Shine a Shoe: A Gentleman’s Guide to Choosing, Wearing, and Caring for Top-Shelf Styles*. Carkson Potter Publishers New York.

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