BROGUES have come a long way. Invented in the bogs of either Ireland or Scotland, depending on who you believe, they were originally designed for wading about in mud and water – hence the holes, which were designed to let the water run through. When country gents started bringing the style to town, their journey from the fields to the fashionable drawing rooms was underway.

Representing good provenance and classic styling, brogues are in vogue right now – even worn as a casual shoe with jeans. A couple of years ago New Balance went so far as making a brown trainer with brogue-like punching. They’re called the RC576D, and are available only in Japan, more’s the pity. Even skateboard brand Vans do a wing-tip shoe.

But for the City chap, how do you wear a brogue? And when? “A good brogue can go the distance from a board meeting to a night out on the town,” says Nathan Brown, founder of Mayfair shoe brand Lodger.

There are several styles of brogue, he explains: the wing-tip, the half-brogue and the austerity brogue. The wing-tip is the classic brogue with the sweeping extensions along the side of the shoe that look from the top like a bird’s wings. The half-brogue, a more old-fashioned style, has a straight toe-cap across the front of the shoe. The austerity brogue has no punching, as the little holes are called. Apparently this is because you need more leather to place under the punches, and during the war a leather shortage led to brogues without holes.

The punching is of course the most notable thing about a brogue. The pattern of the punching is called the “medallion” and all shoe-makers design their own. In recent years they have become more decorative and now people play about with the shapes – Oliver Sweeney, for example, puts an OS into his.

The traditional, chunky brogue is best with a full-cut bespoke suit – it can look over-the-top with a modern slim-fit suit – but now people like Paul Smith are making skinnier versions for a more fashion–focused look.

In terms of colours, you are talking the traditional brown for the country, black for town, says Steve Murdoch – general manager for Crockett & Jones, a fifth-generation shoe-maker based in Northampton with shops in Burlington Arcade, Jermyn Street and the Royal Exchange.

“The black brogues are considered a smart shoe for business, while the brown brogue is a casual weekend shoe,” he says. However, he adds that the dark reddish-brown cordovan shoe is also a good option with this style. Brown agrees – he wears this colour, which he also calls oxblood, himself. Partly it’s the flexibility – “a rich coloured brogue can be paired with an intensely-coloured blue or grey suit, but you can always wear it with jeans and a sports coat as well” – but he also says that this is a style where you can show a bit of personality and that this can help to add some “gravitas”. Maybe best avoid those bogs, though.