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Dress Shoes for Men


Avoid brown in town (and after 6.00pm). British construction beats Italian. 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 bootmakers 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 shoe-pedia so that you can shop our Edward Green, George Cleverley, John Lobb, Cheaney, Berluti 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, here are the 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: Derbies 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: Mr Fred Astaire). Go with a cap toe and you’ll be at home in any boardroom. Originating in Scotland, Oxfords are sometimes called “Balmorals” after Balmoral Castle.


Derbies have open laces (the facing is open at the bottom), giving a more robust and versatile feel – the trusty Land Rover to the elegant Audi A8 Oxford. They come in colours ranging from Cognac and oxblood to other reds and browns (and we like to wear brown in town à la Mr 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 L.L.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. 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.

Monk Strap
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 monks are more understated and timeless (try chocolate brown suede), while the two straps of a double monk 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. They have been popularised in recent years by the likes of Pitti Uomo regular Mr Lino Ieluzzi.
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 should you want to wear them as often as Mr Michael Jackson did. Classic styles include the penny, tassel and Gucci loafer.

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 Mr 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.Chelsea
With quaint, equestrian origins dating back to Queen Victoria, Chelsea boots – popularised by The Beatles and other British Invasion bands in the 1960s – is 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 Mr Sammy Davis Jr or Austin Powers). Whether you’ve investing in Saint Laurent or John Lobb, you can team them with Savile Row tailoring as easily as you can slim jeans and a leather jacket.

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