Even for men who live in trainers, there’s a certain excitement that comes with stepping into ‘proper’ shoes. Particularly when they’re as storied as the brogue. The style’s distinctive perforations were designed initially as an escape valve for bog water, favored by Irish farmers who spent half their working day stomping through submerged fields.

For much of its life, the best brogues for men stayed firmly in the country; appropriate for hikes, never in town. But in the 1930s, the then-Prince of Wales (future king and style icon) adopted the style for golf, pairing his with a grey lounge suit. The holes were suddenly seen as decorative, not practical, and the brogue went on to become a flamboyant staple in jazz clubs.

Although broguing is most common on Oxford shoes, because the moniker refers to the perforations, not the construction, examples are almost limitless. Heritage British shoemaker Grenson even teamed up with Boston-based New Balance on a brogued sneaker, all holey, caramel leather, but with a running shoe’s midsole and shape.

This variety has helped the brogue become one of the most versatile shoes in men’s wardrobes; depending on the construction and level of decoration (as a rule of thumb, the busier the toe cap, the less formal the shoe), it wears with everything from a suit to shorts, everywhere from the office to beer gardens.

That longevity and versatility means it’s worth investing – no other type of shoes in your wardrobe will get as many outings or last as long, which brings the cost-per-wear down to pence.

Ready to put your best foot forward? Here’s what to look for when shopping for your next pair and all the brands worthy of your hard-earned.

4 Key Types Of Brogue

Wingtip

Not all brogues are wingtips, and not all wingtip shoes have to be brogues. Confusing? A wingtip is defined by the ‘W’ or wing-shaped piece of leather that overlaps the toe area of the shoe – as long as it has that, it’s a wingtip. However, most brogues tend to feature it, hence the confusion. Also known as a full brogue they come in all manner of shapes, from more casual Derby shoes to suit-ready Oxfords and even two-tone styles that wouldn’t look out of place on the feet of a 1950s jazz band.