STYLE GUIDE

Style Guide

Having a great pair of dress shoes in your closet is not a luxury, it’s a necessity. Even men who default to casual shoes and sneakers will eventually need to suit-up. Opportunity favors the prepared.

This guide is intended to help you make a wiser choice on your next shoe purchase. Once you understand the differences between the options available, you will be half-way to looking your best at any event, interview, meeting, or date that requires a formal shoe.

In order to understand a particular style, you should first understand the components that make up a dress shoe. Working from front to back, a dress shoe is divided into four parts: toevampfacing, and quarter. It is the placement and construction of these pieces that help give a dress shoe its individuality.

Type Of Dress Shoes

Men Brogues are often mistaken as a style of shoe in itself, whereas the term brogue actually refers to the pattern of the perforation made in the shoe. A Derby shoe or an Oxford shoe can have "brogueing". The perforations were originally made to let out water in wet terrain yet have now become solely a decorative addition to a shoe.

There are several styles of brogueing:

  • Full Brogues: With brogueing on the entire shoes and wingtips
  • Semi Brogues: Brogueing is seen on only half the shoe
  • Quarter Brogues: Brogueing is feature on only the end of the shoe
  • Longwing Brogues: Brogueing is featured down the shoe lengthwise rather than horizontally across the shoe
More

The Oxford is by far the most classic of dress shoes that you will come across, instantly recognisable and the best starting point if you’re looking for a wardrobe staple. Also one of the most versatile of shoes that can be worn in any situation or with any combination of casual or formal wear. The name Oxfords originates from Oxford students opting for this style of shoe over the Oxonians that were the preferred choice in the 1800’s.

There are several variations on the Oxford, but whatever variation you choose, a pair of black or brown Oxfords is a classic that you can’t go wrong with, whilst for dress or more formal wear, a pair of patent Oxfords will finish your outfit with an extra dash of sophistication.

The Oxford shoe can come in 4 different styles:

  • The Cap Toe Oxford
  • The Wingtip Oxford
  • The Plain Toe Oxford
  • The Whole Cut / One Piece Oxford
More

The difference between a Derby and an Oxford is very slight and often Derbys are, understandably, confused with Oxfords.

The difference in the shoes lies at the ‘top’ of the shoe. The Derby shoe has stitching on the vamp, right across the shoe, whereas the Oxford has its tabs sewn under the front panels. The type of shape allows for a wider fit, making the shoe more practical, comfortable and more suitable for everyday wear.

There are again several variations on the style of shoes:

  • The Cap Toe Derby
  • The Wingtip Derby
  • The Plain Toe Derby
More

Men Brogues are often mistaken as a style of shoe in itself, whereas the term brogue actually refers to the pattern of the perforation made in the shoe. A Derby shoe or an Oxford shoe can have "brogueing". The perforations were originally made to let out water in wet terrain yet have now become solely a decorative addition to a shoe.

There are several styles of brogueing:

  • Full Brogues: With brogueing on the entire shoes and wingtips
  • Semi Brogues: Brogueing is seen on only half the shoe
  • Quarter Brogues: Brogueing is feature on only the end of the shoe
  • Longwing Brogues: Brogueing is featured down the shoe lengthwise rather than horizontally across the shoe
More

The Oxford is by far the most classic of dress shoes that you will come across, instantly recognisable and the best starting point if you’re looking for a wardrobe staple. Also one of the most versatile of shoes that can be worn in any situation or with any combination of casual or formal wear. The name Oxfords originates from Oxford students opting for this style of shoe over the Oxonians that were the preferred choice in the 1800’s.

There are several variations on the Oxford, but whatever variation you choose, a pair of black or brown Oxfords is a classic that you can’t go wrong with, whilst for dress or more formal wear, a pair of patent Oxfords will finish your outfit with an extra dash of sophistication.

The Oxford shoe can come in 4 different styles:

  • The Cap Toe Oxford
  • The Wingtip Oxford
  • The Plain Toe Oxford
  • The Whole Cut / One Piece Oxford
More

The difference between a Derby and an Oxford is very slight and often Derbys are, understandably, confused with Oxfords.

The difference in the shoes lies at the ‘top’ of the shoe. The Derby shoe has stitching on the vamp, right across the shoe, whereas the Oxford has its tabs sewn under the front panels. The type of shape allows for a wider fit, making the shoe more practical, comfortable and more suitable for everyday wear.

There are again several variations on the style of shoes:

  • The Cap Toe Derby
  • The Wingtip Derby
  • The Plain Toe Derby
More

A shoe with a monk strap is similar in shape and construction to an Oxford but in place of an eyelet closure, the monk strap has a wide swath of leather fastened across the front of the shoe. This is the “strap,” which is fastened with either a single or double-buckle closure. The shoe takes its name from the monks who originally donned them. The simple closed-toe design provided greater protection than the sandals traditionally worn by men in the orders.

How “formal” is a monk strap? All else being equal, the style itself lies somewhere between the Oxford and the derby. This classic alternative to laced dress shoes adds a certain panache to any outfit. While this has not always been the case, the monk strap is now regarded as a very versatile style of shoe style. It can be worn with cuffed jeans, or with the most dapper of suits. Monk strap attracts attention and may at times become the focal point of an ensemble. Monk strap shoes are often crafted out of leather or suede, and will sometimes decorative broguing.

More

The Chelsea boot originated in Victorian England, reputedly with shoemaker J. Sparkes-Hall  (boot maker to the Queen Victoria). Then as now, the boots’ elastic gussets allowed for them to be pulled-on and slipped-off with ease, without compromising the refined silhouette of a laced boot. Indeed, the absence of laces contributed to their neat shape. The Chelsea boot became the practical alternative to the rigid Victorian boots of the age and quickly recommended themselves to the equestrian set. There was an uptick in sales the 1960’s when Mods took them from the paddocks to the pavements. Victorian naturalist Charles Darwin might have had a fondness for beetles, but The Beatles had a fondness for Chelsea boots. Thanks in part to blokes like them, the style remains popular today.

These boots are ankle length with rounded toes and low heels. The vamp and the quarters meet near the ankle and are joined by an elastic gusset. The Chelsea boot owes its clean, tidy look to the fact that – in dressier versions – the vamp and quarters are made from a single piece of leather. This keeps the stitching to a minimum. Classic Chelsea boots are absent decorative flourishes or embellishments. Their simplicity puts them in a class all their own: jeans get an upward lift, and traditional-style suits gain an edge.  If you purchase suede Chelsea boots, wear them only as part of a casual or smart-casual ensemble.

More

The Chukka has origins in the game of polo: it is the unit of time by which polo matches are measured. (A typical chukka is seven minutes long, and a polo match consists of four, six, or eight chukkas.)  Some have said that chukkas resemble shorter versions of the boots worn by polo players, but it is claimed also that they were intended to be a more comfortable version of polo boots that players could wear after the game — think the original Uggs and surfers.

Chukkas are ankle-length boots with two to three pairs of eyelets on each side for a lace-up closure. These eyelets allow for a snug fit around the ankle which, unlike regular boots, will not disrupt the shape of one’s trouser-bottoms. Chukka boots generally have a rounded toe, minimal stitching, and open lacing (similar to the derby). They are traditionally made of soft suede, but nowadays there are many versions from which to choose.

Chukkas are not to be confused with desert boots. Desert boots are a much more casual version of a Chukka boot and have a nearly identical shape. They are distinguished by soles that are not made of leather.

These are the least formal of the shoes we are discussing. They would not be appropriate for anything except casual attire, although pairs in high-quality leather compliment a smart-casual ensemble. Both chukkas and desert boots are exceptional.

More

A shoe with a monk strap is similar in shape and construction to an Oxford but in place of an eyelet closure, the monk strap has a wide swath of leather fastened across the front of the shoe. This is the “strap,” which is fastened with either a single or double-buckle closure. The shoe takes its name from the monks who originally donned them. The simple closed-toe design provided greater protection than the sandals traditionally worn by men in the orders.

How “formal” is a monk strap? All else being equal, the style itself lies somewhere between the Oxford and the derby. This classic alternative to laced dress shoes adds a certain panache to any outfit. While this has not always been the case, the monk strap is now regarded as a very versatile style of shoe style. It can be worn with cuffed jeans, or with the most dapper of suits. Monk strap attracts attention and may at times become the focal point of an ensemble. Monk strap shoes are often crafted out of leather or suede, and will sometimes decorative broguing.

More

The Chelsea boot originated in Victorian England, reputedly with shoemaker J. Sparkes-Hall  (boot maker to the Queen Victoria). Then as now, the boots’ elastic gussets allowed for them to be pulled-on and slipped-off with ease, without compromising the refined silhouette of a laced boot. Indeed, the absence of laces contributed to their neat shape. The Chelsea boot became the practical alternative to the rigid Victorian boots of the age and quickly recommended themselves to the equestrian set. There was an uptick in sales the 1960’s when Mods took them from the paddocks to the pavements. Victorian naturalist Charles Darwin might have had a fondness for beetles, but The Beatles had a fondness for Chelsea boots. Thanks in part to blokes like them, the style remains popular today.

These boots are ankle length with rounded toes and low heels. The vamp and the quarters meet near the ankle and are joined by an elastic gusset. The Chelsea boot owes its clean, tidy look to the fact that – in dressier versions – the vamp and quarters are made from a single piece of leather. This keeps the stitching to a minimum. Classic Chelsea boots are absent decorative flourishes or embellishments. Their simplicity puts them in a class all their own: jeans get an upward lift, and traditional-style suits gain an edge.  If you purchase suede Chelsea boots, wear them only as part of a casual or smart-casual ensemble.

More

The Chukka has origins in the game of polo: it is the unit of time by which polo matches are measured. (A typical chukka is seven minutes long, and a polo match consists of four, six, or eight chukkas.)  Some have said that chukkas resemble shorter versions of the boots worn by polo players, but it is claimed also that they were intended to be a more comfortable version of polo boots that players could wear after the game — think the original Uggs and surfers.

Chukkas are ankle-length boots with two to three pairs of eyelets on each side for a lace-up closure. These eyelets allow for a snug fit around the ankle which, unlike regular boots, will not disrupt the shape of one’s trouser-bottoms. Chukka boots generally have a rounded toe, minimal stitching, and open lacing (similar to the derby). They are traditionally made of soft suede, but nowadays there are many versions from which to choose.

Chukkas are not to be confused with desert boots. Desert boots are a much more casual version of a Chukka boot and have a nearly identical shape. They are distinguished by soles that are not made of leather.

These are the least formal of the shoes we are discussing. They would not be appropriate for anything except casual attire, although pairs in high-quality leather compliment a smart-casual ensemble. Both chukkas and desert boots are exceptional.

More

The loafer is a moccasin-inspired shoe that is most recognizable for being a slip-on style. The loafer was originally intended as a casual house slipper made for King George VI of England. The loafer was neither acknowledged nor popular as a casual shoe until the King’s slippers crossed the pond. Manufacture of the loafer in the United States was underway in earnest by the 1930’s. It kept its status as a casual-only shoe until the 1960’s when American businessmen and lawyers began wearing loafers with suits. In 1966, Gucci introduced the bit loafer. This variant features a metal strap (in the shape of a horse’s bit) across the instep. Gucci’s innovation further elevated the loafer’s status as formal footwear — or at least confirmed that this was not strictly casual.

More

The loafer is a moccasin-inspired shoe that is most recognizable for being a slip-on style. The loafer was originally intended as a casual house slipper made for King George VI of England. The loafer was neither acknowledged nor popular as a casual shoe until the King’s slippers crossed the pond. Manufacture of the loafer in the United States was underway in earnest by the 1930’s. It kept its status as a casual-only shoe until the 1960’s when American businessmen and lawyers began wearing loafers with suits. In 1966, Gucci introduced the bit loafer. This variant features a metal strap (in the shape of a horse’s bit) across the instep. Gucci’s innovation further elevated the loafer’s status as formal footwear — or at least confirmed that this was not strictly casual.

More

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