If you’ve ever scratched your head over the difference between an oxford and a Derby shoe, or if you can’t tell a longwing from a cap toe, fret not. The world of the men’s dress shoe is a sharp, sophisticated and beautiful one, but it’s also a bit confusing. The following guide will, however, help you tell various styles apart.

The Oxford, or ‘Balmoral’

This is the quintessential dress shoe, and the one that you need to begin your collection with. Its singular characteristic is its ‘closed lacing’ construction, which gives it a slim, formal look. Oxfords go well with pretty much anything, and we recommend getting a ‘cap toe’ pair. To stand out, you could try the ‘whole cut’ Oxford, which is made of a single piece of leather.

The Derby, or ‘Blucher’

Derbys and Oxfords are often mistaken for one another, due to their similar construction styles. The key difference is in the Derby’s ‘open lacing’, which gives it a more casual, wider look — it’s also more comfortable than an Oxford. A plain toe Derby is a safe bet, but you can go with a wingtip pair, for a little more oomph.

The Loafer

Starting off life as a moccasin-like house slipper for royalty, the loafer is now an essential item in your shoe collection. At one time, they were strictly casual shoes, but it’s now acceptable to wear a great pair of them with a nice suit (but not to a business meeting). Loafers have some kind of decoration on the front, by way of things like tassels or metal strips. The driving shoe is also a loafer, and has a softer construction, with a rubber sole. These shoes go with anything, so make sure you have a pair.

The Monk Strap

These attractive shoes lie between Oxfords and Derbys in terms of their degree of formality. They’re characterized by the absence of eyelets and laces — instead, you’ll find a wide strap on the front, with either one or two buckles to fasten it on the side. Monks are very versatile, and you can dress them up or down.

The Dress Boot

This is essentially an Oxford with a long shaft, and is a great choice as a pair of shoes that can double up for formal and casual occasions. Dress boots usually have a bit of decoration by way of broguing, and they come in a variety of colours and textures.

The Chukka Boot

Named after a quarter of polo, or “chukker”, this is a very comfortable and versatile boot. It’s ankle-length, with Derby-style open lacing that gives you a firm fit around the ankles. These are usually clean, no-fuss designs, often made of suede, and they go well with almost any sort of smart casual or business formal wear.

The Pump

These are seen rarely today, but you will sometimes find the classic ‘Opera’ pump on the feet of someone who is willing to stand out. These are eveningonly shoes, and are made of patent leather, with a bow across the front.

The Spectator

Also known simply as two-tone shoes, Spectators are shoes that have two distinct colours. They can be Oxfords, Derbys, Monks or even loafers, and can come in a variety of colours and textures. Wearing a pair of these will guarantee you attention, but you have to be careful to match them properly to your outfit.

The Chelsea Boot

The Beatles did Chelsea boots a world of good when they began wearing them regularly back in the 1960s, but they’ve been around longer than that. Characterised by a clean, no-fuss front, elastic sides (for ease of use) and a low heel, these boots are very versatile. A black or brown pair will add a great deal to your shoe collection.

Toe Styles

Plain toe: The front of the shoe is left clean.

Cap toe: A horizontal stitch across the toe section, as in a cap toe Oxford.

Medallion: A plain toe with a small brogue decoration at the front.

Wingtip: Features a winged cap with its peak in the middle of the toe; usually has broguing.

Apron toe: Has a seam starting in the centre of the shoe, around the toe, which ends on the other side.

Types of Broguing

Broguing is the decorative perforation you’ll see on many dress shoes. It is usually done in the following ways.

Full brogue/wingtip: Decorative broguing on the front and sides, with a winged cap.

Semi/half brogue: Broguing is seen along the sides and on a cap toe, with perhaps a medallion.

Longwing: The shoe’s peaked toe broguing extends down the sides and reaches the middle seam at the back. Usually seen on a Derby.

Quarter brogue: Broguing is seen only along the cap toe.