STYLE
In order to be truly at ease and truly well-dressed, a gentleman needs to have his shoes made by
hand. The process is long and ruinously expensive. To have a ‘last’ (the shoemaker’s wooden
model of the foot) made to the shape of one’s own foot, and then to have that first pair of shoes or
boots crafted to a state of bliss, and take between three to six months.
Custom-made shoes are a true investment. If treated with due respect and returned for re-soling
when necessary, they literally last a lifetime. Natural leather after 20 years of wear and care attains
a state of grace that mere words cannot describe.
This having been said, it is a fact that ready-made shoes have made great strides and there are
establishments adept at making shoes that appear to be hand-made. The rule is, buy the best you
can afford, or better still, cannot quite afford. There is no fate worse than to be found out wearing
cheap shoes.
When it comes to choice of colour, the gentleman needs to be circumspect. The ancient Roman
senators wore black shoes, and little has changed in 2,000 years. The classic spectrum reaches
only from black to brown, with Bordeaux, perhaps, on the outer limits. Black alone is proper for
evening. Defy at your peril the maxim of the English gentleman: “Never wear brown after six.”
Blue is acceptable, for leisure pursuits. Two-toned shoes (black and white; blue and white; brown
and white) are strictly for the golf course or other sports place.
FORMAL SHOES
The formal shoe is required to be plain, black, and without a stitch of decoration, or perforation for
that matter. It is made of fine polished calf or patent leather, and may be slip-on or laced.
The low-heeled, slip-on ‘pump’ with a flat bow dates so far back that the origin of the name has
been lost. It was standard for grand receptions and balls when breeches were part of formal wear.
Laced shoes were accepted after the First World War. Patent leather was preferred, but plain calf
was increasingly seen from the 1960s.
OXFORD
The Oxford shoe is nowadays the classic companion of the business suit. Clean-lined, it comes in
several sub-styles with historical associations. The ‘bal’, short for Balmoral, is a closed-throat shoe
with laced front, and recalls the 19th-century boot of that name. The ‘blucher’ has an open-throat
front, as did the boot named after the Prussian general who shared with Wellington the victory of
Waterloo. The ‘gillie’ is a tongue-less Oxford, with lacing across the instep.
DERBY
This is basically an Oxford in reverse, inasmuch as the quarters and facings, which carry the lace
eyelets, are stitched on top of the vamp, or upper. The seams are curved and the effect is more
sporty.
WING-TIP
In contrast to the timeless, simple elegance of other classic styles, the Wing-tip is an exercise in
intricate decoration. The name derives from the shape of the toe-cap, likened to the spread wings
of a bird. This familiar style of the businessman originated with the elegantly curved toe-cap of a
Victorian ladies’ boot .
THE BROGUE
Tamed from its origins in the Scottish Highlands, the brogue is a Wing-tip Oxford with perforations
on the tip and border seams. It traces it ancestry to a version of the Highland brogue introduced in
about 1905.
‘Brogueing’, or punching a pattern of tiny holes into the upper and double-stitching the seams,
became a popular form of decoration, and brogues with fringed tongues were a favourite golf shoe
in the 1920s.
Nowadays, a distinction is drawn between the Full Brogue and the Half-Brogue. The Full-Brogue’s
perforation and decoratively-stitched seam runs right around, from toe-cap to heel. The seam of the
Half-brogue dips to the sole, leaving the back unperforated.
MONK
A charming legend has it that a 15th-century monk was first to create such a shoe with
characteristic strap and buckle over the instep. In fact. Buckled boots and shoes date from the 17th
century, while it was not until the 1930s that the ‘monk’, or ‘monk-front’, style became popular as a
welcome change from the Oxford.
MOCCASIN
This ‘loafer’, or ‘slip-on’, merits a place in any gentleman’s wardrobe, always provided that it is mad
e from quality leather by an able craftsman.
The name moccasin is of course associated with the North American Indian, whose soft and sturdy
deerskins with designs distinctive to individual tribes had ritual as well as practical value. Curiously,
we owe its modern popularity to quite another culture- that of the reindeer-herding Lapps of
northern Scandinavia.
The story begins with Norwegian fishermen using their spare time to stitch together peasant shoes,
some of which went on sale in London, where they were discovered by American tourists. There
were two kinds, slip-ons called ‘Weejuns’ and a lace-up known as the ‘Norwegian-front’. Americans
had no doubts over what to call them and by the mid-1930s the moccasin manqué was, according
to Men’s Wear, the “real man’s shoe for a man’s purpose in every conceivable situation and for
every need”.
The need reached upwards, so that by the 1960s a polished black moccasin was fully acceptable
as a complement to the suit in every situation. Moccasins come in various styles, such as the Tassel
Loafer and the fringe-flapped Kiltie. More useful if only because it is plainer is the Pennyloafer,
whose little slit in the saddle is said to be the place to put one’s ‘last penny’
BOAT SHOE
Here is a good example of footwear evolution. With its water-repellent, oiled calf leather, rawhide
lacing and non-slip soles for safety on slipper decks, the boat shoe was designed for the specific
purpose made clear by its name. So much practicality coupled with a distinctive appearance and
elite ‘yachting’ associations has made it a universal item of sporty footwear.
The deck shoe has also come ashore, for much the same reasons. It is made of tightly-woven air-
permeable canvas and has soles like those of the boat shoe. It is useful for any leisure activity in
warm weather. It may be worn with casual linen trousers or quality jeans.
In order to be truly at ease and truly well-dressed, a gentleman needs to have his shoes made by
hand. The process is long and ruinously expensive. To have a ‘last’ (the shoemaker’s wooden
model of the foot) made to the shape of one’s own foot, and then to have that first pair of shoes or
boots crafted to a state of bliss, and take between three to six months.
Custom-made shoes are a true investment. If treated with due respect and returned for re-soling
when necessary, they literally last a lifetime. Natural leather after 20 years of wear and care attains
a state of grace that mere words cannot describe.
This having been said, it is a fact that ready-made shoes have made great strides and there are
establishments adept at making shoes that appear to be hand-made. The rule is, buy the best you
can afford, or better still, cannot quite afford. There is no fate worse than to be found out wearing
cheap shoes.
When it comes to choice of colour, the gentleman needs to be circumspect. The ancient Roman
senators wore black shoes, and little has changed in 2,000 years. The classic spectrum reaches
only from black to brown, with Bordeaux, perhaps, on the outer limits. Black alone is proper for
evening. Defy at your peril the maxim of the English gentleman: “Never wear brown after six.”
Blue is acceptable, for leisure pursuits. Two-toned shoes (black and white; blue and white; brown
and white) are strictly for the golf course or other sports place.
FORMAL SHOES
The formal shoe is required to be plain, black, and without a stitch of decoration, or perforation for
that matter. It is made of fine polished calf or patent leather, and may be slip-on or laced.
The low-heeled, slip-on ‘pump’ with a flat bow dates so far back that the origin of the name has
been lost. It was standard for grand receptions and balls when breeches were part of formal wear.
Laced shoes were accepted after the First World War. Patent leather was preferred, but plain calf
was increasingly seen from the 1960s.
OXFORD
The Oxford shoe is nowadays the classic companion of the business suit. Clean-lined, it comes in
several sub-styles with historical associations. The ‘bal’, short for Balmoral, is a closed-throat shoe
with laced front, and recalls the 19th-century boot of that name. The ‘blucher’ has an open-throat
front, as did the boot named after the Prussian general who shared with Wellington the victory of
Waterloo. The ‘gillie’ is a tongue-less Oxford, with lacing across the instep.
DERBY
This is basically an Oxford in reverse, inasmuch as the quarters and facings, which carry the lace
eyelets, are stitched on top of the vamp, or upper. The seams are curved and the effect is more
sporty.
WING-TIP
In contrast to the timeless, simple elegance of other classic styles, the Wing-tip is an exercise in
intricate decoration. The name derives from the shape of the toe-cap, likened to the spread wings
of a bird. This familiar style of the businessman originated with the elegantly curved toe-cap of a
Victorian ladies’ boot .
THE BROGUE
Tamed from its origins in the Scottish Highlands, the brogue is a Wing-tip Oxford with perforations
on the tip and border seams. It traces it ancestry to a version of the Highland brogue introduced in
about 1905.
‘Brogueing’, or punching a pattern of tiny holes into the upper and double-stitching the seams,
became a popular form of decoration, and brogues with fringed tongues were a favourite golf shoe
in the 1920s.
Nowadays, a distinction is drawn between the Full Brogue and the Half-Brogue. The Full-Brogue’s
perforation and decoratively-stitched seam runs right around, from toe-cap to heel. The seam of the
Half-brogue dips to the sole, leaving the back unperforated.
MONK
A charming legend has it that a 15th-century monk was first to create such a shoe with
characteristic strap and buckle over the instep. In fact. Buckled boots and shoes date from the 17th
century, while it was not until the 1930s that the ‘monk’, or ‘monk-front’, style became popular as a
welcome change from the Oxford.
MOCCASIN
This ‘loafer’, or ‘slip-on’, merits a place in any gentleman’s wardrobe, always provided that it is mad
e from quality leather by an able craftsman.
The name moccasin is of course associated with the North American Indian, whose soft and sturdy
deerskins with designs distinctive to individual tribes had ritual as well as practical value. Curiously,
we owe its modern popularity to quite another culture- that of the reindeer-herding Lapps of
northern Scandinavia.
The story begins with Norwegian fishermen using their spare time to stitch together peasant shoes,
some of which went on sale in London, where they were discovered by American tourists. There
were two kinds, slip-ons called ‘Weejuns’ and a lace-up known as the ‘Norwegian-front’. Americans
had no doubts over what to call them and by the mid-1930s the moccasin manqué was, according
to Men’s Wear, the “real man’s shoe for a man’s purpose in every conceivable situation and for
every need”.
The need reached upwards, so that by the 1960s a polished black moccasin was fully acceptable
as a complement to the suit in every situation. Moccasins come in various styles, such as the Tassel
Loafer and the fringe-flapped Kiltie. More useful if only because it is plainer is the Pennyloafer,
whose little slit in the saddle is said to be the place to put one’s ‘last penny’
BOAT SHOE
Here is a good example of footwear evolution. With its water-repellent, oiled calf leather, rawhide
lacing and non-slip soles for safety on slipper decks, the boat shoe was designed for the specific
purpose made clear by its name. So much practicality coupled with a distinctive appearance and
elite ‘yachting’ associations has made it a universal item of sporty footwear.
The deck shoe has also come ashore, for much the same reasons. It is made of tightly-woven air-
permeable canvas and has soles like those of the boat shoe. It is useful for any leisure activity in
warm weather. It may be worn with casual linen trousers or quality jeans.
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How to dress like a gentleman- A guide on the styles of shoes for the true gentleman.
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