How to tell the difference between several kinds of men's dress shoes

From Oxfords to Derbys, here is the guide to different men's shoes which may help you tell the difference

The old cliché about being able tell a lot about a man by his shoes may be stretching things a bit, but that’s no reason to not arm yourself with as much knowledge as you can about them. I speak with the almost fanatical bias of a person who can barely stop himself from buying a new pair of shoes every month – some say I need help – but in my opinion, every man who wants to look good needs to own good looking and well crafted dress shoes. If they’re bespoke, that’s even better. This guide should help, in that regard.

Oxfords

 

If there’s one pair that any collection should have, it’s the Oxford. This is the all-time classic dress shoe. You’ll be able to identify it by its closed lacing construction, which gives it a slim structure. These shoes pair well with virtually any ensemble. My suggestion is to get a black pair, with a cap toe (see: toe styles).

Oxfords

Derbys

 

These shoes and Oxfords are often confused for one another because they look quite similar – with one major difference. Derby shoes have a more open lacing style, which gives them a wider look that is more casual. Derbys in black or tan, with plain toes, are always a safe bet.

Derbys

Loafers

 

These shoes began life as footwear that royalty wore around their palaces, but they’re now ubiquitous. Once strictly for casual occasions, they can now be worn with a suit, but obviously not to a board meeting. These shoes sometimes have tassels or bits of metal on their fronts. Regardless of decoration, they go with everything, so you should have a pair.

Loafers

Monk straps

 

These shoes don’t have any eyelets or laces; rather, they have a strap on the front, with either one or two buckles down the side. Falling between Oxfords and Derbys on the formal shoe scale, monks are very stylish and versatile.

Monk straps | Photo:  istock

Dress boots

 

These are Oxfords with a long shaft, and can quite acceptably be worn even to the most formal occasions. They usually have some broguing on them.

Dress boots

Chukka boots

 

These versatile and comfortable boots are named after a quarter – or “chukker” -- of polo. They are ankle-length, and have Derby-type lacing, fitting snugly around the ankles. A pair made of suede will go well with almost any sort of smart-casual or business formal wear.

Chukka boots

Spectators

 

These are Oxfords, Derbys, Monks (or even loafers) that have two or more distinct colours on them. They come in a range of colours and textures ranging from sober to OTT, so you have to match them carefully with what you’re wearing.

Spectators

Chelsea boots

These are slip-on boots that are characterised by a clean front, elastic sides and a low heel. They are among the most versatile shoes around, and are well worth including in your collection.

ENDNOTE

While these styles are easily available, onehugestep.com and elitify.com have a good range

Toe styles

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

Cap toe: This is a horizontal stitch across the toe section.

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

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

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

Broguing styles

Broguing (derived from the Gaelic word for "shoe") is the decorative perforation you’ll see on many dress shoes.

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

Semi/half brogue: Broguing along the sides and on a cap toe.

Longwing: The peaked toe broguing extends down the sides and reaches the middle seam at the back; usually seen on Derby shoes.

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