Avoid brown in town. Or after 6.00pm. And never do business with a man in loafers. These are some of the shoddy truisms our grandfathers taught us as callow lads. We also remember the intoxicating confusion of entering a proper bootmaker’s for the first time. The experience was not that different to being hungry and in need of a stiff drink in a foreign land. Staring at the array of bench-made shoes as a well-meaning salesman prattled on was as disconcerting as that Scandinavian misadventure when we thought we ordered a steak and received cold mackerel.

Based on the theory that an educated consumer is the best customer, we’ve created this comprehensive guide, so that you can shop our Edward Green, George Cleverley, John Lobb, Berluti, our own Mr P. and other shoes knowing the rules, history and definitions that have existed since the factories of Northampton, England, first kicked into action hundreds of years ago.

Although contemporary trends have relaxed the traditions somewhat, there are key footwear facts and tips that any well-shod man should know. Whether you want to avoid a red card for donning bluchers with black tie or are in the market for amassing a comprehensive shoe collection, consult our shoe encyclopedia, below.

Formal lace-up shoes can be split into two sorts: Derby shoes and Oxfords. Both include a vamp – the front of the shoe attached to the quarters (the upper section that covers the sides and back), a low heel and often a Goodyear-welt construction. With Oxfords, the “facing” (where the eyelets are located) is sewn under the vamp. A closed lace gives a sleeker appearance, so a decent pair of black plain-toe Oxfords is your go-to dress shoe. (Buy them in patent leather for extra sophistication. See: Fred Astaire.) Opt for a cap toe and you’ll be at home in any boardroom. Originating in Scotland, Oxfords are sometimes called “Balmorals” after Balmoral Castle.

Derby shoes have open laces (the facing is open at the bottom), giving a more robust and versatile feel – the trusty old-school Land Rover Defender to the Oxford’s elegant Audi A8. They come in colours ranging from cognac and oxblood to other reds and browns (and we like to wear brown in town à la Jarvis Cocker) and can be teamed with a suit, jeans or chinos. If you’re a little more traditional, adhere to their rustic roots and stick to trousers and a sports jacket. Sometimes called bluchers (especially in the US by New England preppies who grew up wearing a particular LL Bean model), there are subtle differences between the two, but this is best explained over a pint.

If we were really picking holes – literally in this case – we would say that “brogue” refers to a detail: the perforations designed to drain water from the feet of our Gaelic ancestors when crossing boggy terrains. However, whether in an Oxford or Derby style, a brogue is very much a shoe in its own right. Wingtips are a brogue with a decorative detail on an extended toecap. Cap toes are brogues with a plain toe, although often with perforations along the edge of the cap. Try box calf leather, suede or Scotch grain, depending on how relaxed you want to go.

Despite the name, there’s nothing slovenly about slip-ons, yet they certainly offer a more laid-back look. The origin is disputed, but King George VI is said to have wanted an indoor shoe for his country house back in 1926. Low sitting and without laces, they have a moccasin-like upper, often with a piece of leather straddling the upper (the saddle). Note: no detail on the upper, and the presence of a heel, differentiates the loafer from its cousin, the moccasin. They are commonly Blake stitched, but you can get Goodyear-welted pairs. Classic styles include the penny, tassel and Gucci’s horsebit loafer.

With quaint, equestrian origins dating back to Queen Victoria, Chelsea boots – popularised by The Beatles and other British Invasion bands in the 1960s – are a bona fide rock’n’roll addition to any contemporary shoe collection. Comfortable and sleek, they are characterised by an elasticated gusset on the side (although many styles employ a zip – think Sammy Davis Jr or Austin Powers). Whether you’re investing in SAINT LAURENT, R.M.Williams or John Lobb, you can team them with Savile Row tailoring as easily as you can slim-fit jeans and a leather jacket.

With its bold buckle, this shoe sits comfortably between an Oxford and a Derby in terms of formality, and as a rakish alternative to a lace-up. Single monk straps are more understated and timeless (try chocolate-brown suede), while double monks exude a military feel – and are usually designed with a toecap. Although the style dates back many centuries when monks were looking for an alternative to the sandal, these shoes are favoured by style aficionados looking for something different.

Ankle high, constructed from two bits of leather and with two or three high-lacing eyelets, the chukka is related to the jodhpur boot in polo (a chukka is a period of seven-and-a-half minutes, trivia fans). The chukka is a more casual shoe traditionally made from calfskin leather, but suede or black kid leather are dressier options. Crepe soles on desert boots were introduced by Nathan Clark after he saw what soldiers were wearing on their feet during a trip to Burma in 1941. We prefer ours in brown or tan, and we’d advise not combining a crepe-soled chukka with a suit.

Simplicity usually defines elegance. The cleanest example of a shoe, and often the most formal – whether an Oxford, Derby or Chelsea boot – means no toecap or brogue detail.

This is an extra piece of leather on the toe resulting in a more versatile shoe – especially with a Derby. A cap-toe Oxford is acceptable formal attire, but most likely seen on well-heeled businessmen.

Featuring a pointed toecap that extends along each side of the shoe, these are a less dressy incarnation of the Derby and Oxford (but still business appropriate, in our opinion). From a bird’s-eye view the toe is shaped like a “W” (or an “M”, depending on how you’re admiring your shoes). A brown wingtip works well with tweed, while suede offers a more relaxed choice.

A Derby or Oxford shoe with a perforated, and often serrated, toecap edge, with decorative perforations in the centre of the toecap. Note: no “W” design.

Is it a style, or is it a detail? Here it is defined simply: the combination of a semi-brogue and a classic wingtip.

The same as the semi-brogue but without perforations in the centre of the toecap.

The more outlandish relative of the wingtip, these shoes feature a pointed toecap with broguing that runs the full length of the shoe, meeting at the centre seam of the heel.

An upper cut from one single piece of leather, this makes for the ultimate elegant shoe and something you could easily get married to… or in, should we say. If you take a whole-cut Oxford and throw patent leather into the mix, you’re unlikely to put a foot wrong at a ball or formal party.

Quite simply, this is when the front of the upper is rounded, giving an appearance that is neither square nor pointed.

Slightly rarer than our friend above, a square-toed shoe has a bit more bite. It can look irreverently elegant on an Oxford (George Cleverley does it well) or make a Chelsea boot that little bit meaner.

Common on our old friend the loafer and a style staple among Ivy Leaguers, some consider the tassel a stuffy and unnecessary addition to a moccasin-style shoe. Tassels can make even the hippest of guys look as if they’ve been looting certain parts from their mother’s curtains, but a pop of colour from your socks should help.

This is a tongue of fringed leather affixed onto the vamp of a shoe, which can make your feet look like forms of cephalopod. From monk straps to loafers to chukkas, a kiltie can be attached to many a shoe – but, like adding accessories to your smartphone, you may want to keep it to a subtle minimum, if at all.

A welt is a strip, usually made of leather, stitched to the upper and insole of a shoe that runs around the perimeter of the outsole and serves as an attach point for the sole. A cork (or other porous material) filling allows the shoe to breathe and mould to the shape of your foot. Invented by Charles Goodyear Jr – an American – this technique is the bread and butter of proud English shoemaking and seen by many as the longest-lasting shoe construction (unless you ask the Italians – see below). Goodyear-welted shoes take a while to wear in but remember: good things come to those who wait. They also make it easier to replace the soles, should you have waited too long.

Used commonly in the Italian shoe industry (Tod’s is an exemplary example), the upper is directly stitched to the sole, resulting in lighter shoes both in appearance and weight, with greater flexibility. With no welt, Blake-stitched shoes potentially wear out quicker and the sole is harder to repair for most cobblers. This might explain why several Italian shoemaking families have vast country estates, while we Brits do very well, thank you very much.

This method of attaching a shoe’s sole to its upper was developed, as the name suggests, in Scandinavia. It ensures waterproofness and sturdiness with the addition of a second stitching. The upper is turned outwards rather than folded under the insole, making the welt flush with the sole and upper, creating arguably a superior aesthetic effect for boots and country footwear. A durable yet stiff construction.

Leather is the most elegant material for well-made dress shoes and a single layer results in a sleeker, neater feel, which suits the nature of a plain Oxford, for example. As leather is essentially porous and slippery when wet, copious amounts of rain won’t be your friend – rubber soles, with their added grip, are better if you want (to avoid) a night on the tiles. Tip: shoe trees absorb water between wears, while heel caps aid grip.

More protective and warmer, although potentially less comfortable, double-leather soles are more robust and rustic. Casual or outdoor boots use a double sole to deal with harsher conditions.

Perhaps not the most sophisticated choice (much like a certain album by The Beatles), rubber soles provide extra grip in exchange for less breathability. Not as stiff as leather, rubber can be a popular option when repairs are needed on less formal shoes.

A form of textured rubber that’s lightweight and often seen on the desert boot – part of the chukka family. It can wear quickly, however, and was once associated with lower classes and the military. Should not be worn with a formal suit.

Dainite, a British brand established in 1894, produced rubber soles with added protection and durability: Studded, Ridgeway and Medway designs are popular choices and can be seen on shoes by traditional brands such as Church’s. If you live in inclement climes and wish to hold on to your Derby shoes, it’s no great sin to replace leather with Dainite.

Once upon a time, super-shiny, patent leather was reserved exclusively for wearing with a tuxedo. But as formal and casual become increasingly blurred, you’re as likely to see as many patent shoes on the street as you are at a ball. The permanent finish is traditionally a linseed oil lacquer, but is now commonly achieved with a synthetic coating. Keeping patent-leather shoes for special occasions is a good idea, if only because they crease so easily.

“Smooth” denotes any leather that is devoid of pebbling or noticeable grain, and can be shined with ease. (Here’s how to shine your shoes correctly.)

The most durable part of the hide of an animal is just below the hair – where full grain is obtained. A full-grain pattern resists moisture well and will become malleable and develop a pleasant patina with wear.

Top grain, similar to full grain in appearance, is the second most durable leather. The “split” layer has been separated and the remaining surface sanded and buffed to remove any imperfections.

That nubby Braille-like pattern on leather is full-grain leather embossed by heavy rollers or a pebble-grain plate – a technique often applied to second- or third-quality hide. It can add intrigue to less formal shoes such as loafers or Derby shoes, and is perfect for teaming with tweed.