From the Irish and Scottish countryside to the modern-day wardrobe, with the Prince of Wales, jazz musicians and Elvis Presley in between
First of all came the brog, meaning shoe in Gaelic, from the Old Norse brók, used to refer to something that covered the legs. In the late sixteenth century, in the peat-bogs of Scotland and Ireland, farmers began wearing perforated footwear, which helped water drain away better. Later used by fishermen too, the perforations began to take on characteristic patterns, to ward off ill luck more than anything else: to keep bad luck away and bring good fortune.
Brogues only took on a purely decorative function in the early 20th century, when they entered the elegant-wear wardrobe of both men and women.
They were “released” once and for all from the countryside, for legitimate wear by the aristocracy, thanks to a real arbiter of style, the then Prince of Wales, who wore them as golf shoes in the ’30s.

From the 1930s on, the Prince of Wales, Edward Windsor, would often play golf in shoes featuring brogueing. He set the trend, which is still followed to this day, of never wearing them after 6 p.m.
The two-tone Brogue, also know as the Spectator, was the typical shoe of the so-called “golden age” of jazz. Elvis Presley made it popular among young people in the 1950s, while iconic-model Twiggy made it a trend for women in the 1970s.
Technical matters…
People sometimes wrongly tend to see the Brogue as a shoe style in its own right, when in actual fact, it is a variant, generally applied to the classic Derby and Oxford shoes, as well as to Monk shoes (with buckle fastening).
The perforations are usually made on the seams of the various parts of the upper, alternating holes of a larger diameter with those of a smaller diameter.
A toecap with any kind of design is called a perforated toecap.
The W-shaped decoration on the toecap is called the wingtip. If this is present, we speak of Full-Brogue, otherwise of Semi-Brogue (and Quarter-Brogue for shoes without even any perforation on the toe).
A Full-Brogue with punch hole detailing running all the way around to the back of the shoe is called the Long Wing Brogue.