Anatomy of a Dress Shoe

Dress shoes, structurally, may be the most complex thing you wear every day. In this article, we’ll break down the component parts of a pair of shoes so you can shoe shop like an expert.

Recently on The Gentleman’s Gazette, we’ve discussed the stylistic features that make up a suit and a pair of pants. Continuing further from head to toe, we end up with shoes. When we buy them, we usually choose them first for the style and fit, but rarely for their individual construction.

It’s worth a look at the individual parts of a dress shoe so you can be a smart shopper.

Ace Marks - Basic 4 Shoes
Four basic dress shoe styles for men

The Anatomy of a Dress Shoe

Two Main Parts of a Shoe

In the broadest sense, a shoe is divided into two main parts, the upper, which is everything on top of your foot plus the lining, and the sole, which makes up the underside. Let’s start by taking a look at the upper, the more visible part of the shoe, moving from front to back.

Awaiting lasting
Shoe uppers awaiting lasts

The Toe

The upper is made by stretching leather over a last, a carved form usually made of wood, and leaving it there for some time so that it molds to its shape.

Bespoke lasts and a trial shoe
Bespoke lasts and a trial shoe

It is eventually secured to the sole with either glue or nails. At the very front of the upper, we have the toe, which can either be simple or embellished, perhaps with a medallion.

Beautiful patina and custom medallion and buckle on a bespoke monk strap shoe by Ugolini
Beautiful patina and custom medallion and buckle on a bespoke monk strap shoe by Ugolini

This is a pattern made up of perforations in the leather, which makes it somewhat more casual, an unadorned toe being more formal than one with ornamentation. Toe shape on a shoe can vary, and whether it is rounded, almond shaped, or chiseled, plays an important role in the appearance and visual impression of the shoe as well as how comfortably it fits.

The Vamp

Directly behind the toe is the vamp. This is the area that flexes when you walk and is thus subject to creasing. You never want to apply polish, especially wax polish, to the vamp, as it will dry there and crack when the shoe creases, creating a cloudy and caked appearance.

Though some creasing of the vamp is inevitable simply by virtue of the way your foot flexes, it can be minimized by buying shoes made of quality leather and then by storing them with shoe trees to keep the vamp stretched out.

The vamp is the area where the shoe creases most

The Quarters

After this come the quarters. The quarters include everything on the upper, including where the laces are up to where the leather wraps around the back of the heel; in essence, the quarters are the sides and back of the shoe. The nature of the quarters is what determines the difference between a derby and an oxford lace-up shoe.

An oxford and a derby, when compared, show the two different types of construction of the quarters

On the former, the quarters are stitched over the vamp, creating two flaps that are then tied together with laces; on the latter, you have the opposite, with the vamp stitched over the quarters. This makes for a cleaner, and therefore more formal,  look since there aren’t any top flaps of leather. When tying a derby, there will always be some gapping between the flaps, which is referred to as an open lacing system.

Light Brown Shoelaces Round Waxed Cotton - Made in Italy by Fort Belvedere closeup
An open lacing system featuring light brown shoelaces by Fort Belvedere

On the other hand, the gap on an oxford is minimal, which is why it is referred to as having a closed lacing system.

Close up Red Shoelaces Round Waxed Cotton - Made in Italy by Fort Belvedere
A closed lacing system featuring red shoelaces by Fort Belvedere

The laces themselves are threaded through eyelets, usually five pairs, sometimes four, which are punched through the area known as the facing of the shoe. Beneath the facing, you’ll find the tongue, a piece of leather that looks like its anatomical namesake. We don’t usually think of the tongue of having a specific purpose–it’s just “there”–but it’s actually designed to protect the top of your foot from the pressure of the laces.

Front Angle of Fort Belvedere Round Boot Laces in Dark Green, Royal Blue and Red - Made in Italy
The tongue is designed to give you a smooth feel under the lacing system, which is particularly important on boots

At the back of the shoe is the topline, which is the top edge of the hole into which you put your foot. At the heel, the topline is supported internally by additional leather reinforcement known as the heel counter.

Travel shoe horn with engraved Fort Belvedere Logo
A shoe horn is essential to protecting the integrity of the structure of your shoes

Protecting the heel counter is the reason why you should always use a shoehorn when putting on and taking off dress shoes: jamming your heel against the topline as you force your foot down into the shoe will cause the leather there to buckle and collapse. This can leave permanent wrinkles or deform the area, ruining the fit.

Shoepassion Workmanship
The topline on the back of a pair of Shoepassion shoes: below the leather of the heel is the heel counter to add structure

The Insole

Inside the shoe you have the insole, which in a dress shoe should be made of soft leather. The insole provides comfortable, smooth padding for your foot to rest upon.

Black Insole and Lining
Black Insole and Lining

This footbed contrasts the hard outsole–the lowest part of the shoe–which touches the ground. Between the insole and outsole is the midsole, which can be made up of cork, for cushioning.

Also under the instep of your foot, manufacturers may place a shank–a thin rectangular strip of metal, wood, or fiberglass–that helps to support the foot. The choice of shank material, and whether to use one at all, depends on the brand. For instance, according to a Reddit survey, Crockett & Jones uses wood, Meermin uses steel, and Allen Edmonds doesn’t use anything at all.

The Welt

Forming the transition between the upper and the outsole is the welt. This is a thin strip of leather that protrudes around the edge of the outsole to which the upper is secured.

Breaking in the leather sole of a good year welted chukka boot
A good year welted chukka boot

Connoisseurs of footwear will know that the two ways to do this are with a Goodyear welt or Blake stitching. Goodyear welted shoes, named for a machine originally manufactured by Goodyear, are more expensive because of the way the outsole is attached to the upper, which involves a more complex double-stitch approach. Because of this, they can be resoled fairly easily by a cobbler.

Goodyear Welt Construction
Goodyear Welt Construction

The Blake method, on the other hand, involves a simpler stitching method where the insole, upper and outsole are joined together with a single stitch that, while simple to create is difficult to repair.

Ace Marks - Blake Stitched Shoe with Hand Burnished Patina
A Blake Stitched Shoe with Hand Burnished Patina

Because it is made completely inside the structure of the shoe with a machine, resoling the shoe is difficult if your cobbler doesn’t possess said machine. And, even then, it is a more laborious and potentially more costly process. For this reason, and because the complexity of Goodyear welting is also matched with other higher quality features, a Goodyear welted shoe is usually worth the investment.

Blake Construction
Blake Construction

The Sole

The outsole is the lowermost part of the shoe and has to satisfy the double demands of supporting the full weight of the wearer and standing up to the friction of walking on the ground. In a dress shoe, the outsole is commonly made of leather, which is the most elegant, but Dainite (rubber) is also a popular option for those who want more grip and greater water resistance. The thickness of the leather can vary, with multiple layers of outsole appearing in chunkier country derby shoes like those made by Tricker’s or Church’s in the UK. These may be referred to as “double leather” soles.

Tricker's shoes
Tricker’s chunky Keswick shoe with a double leather sole

With an outsole made of leather there are more opportunities for various structural details that add to its elegance and craftsmanship. One example is a beveled or fiddleback waist.

G&G's characteristic sole with fiddleback waist
A Gaziano & Girling sole with beveled fiddleback waist

This used to be seen only on bespoke shoes, but newer technologies have made it accessible in ready-to-wear models. The waist is the narrowest part of the sole, located between the heel and the ball of the foot, directly below the arch of your foot, just as the waist is the narrowest part of the torso in an ideal physique. Beveling the waist shaves down the leather there and gives it a sharp chiseled appearance. The fiddlehead waist occurs when a beveled waist is extended into a V shape toward the direction of the toe.

EG shoes have distinctively nailed heels. These await finishing.
EG shoes have distinctively nailed heels. These await finishing.

Finally, we have the heel at the bottom rear of the shoe. Like the outsole, the heel can be built up with individual layers of leather or rubber, and sometimes a combination of both. Rubber is usually reserved for the back edge of the heel, as shown in the Gaziano & Girling image above to provide a measure of grip.

A high-quality dress shoe will usually join the rubber to the leather with a dovetailed joint. An additional touch that you may find on the heel is known as the gentleman’s notch or gentleman’s corner.

Gentleman's corner
Gentleman’s notch on the inside corner of the heel

This is a notch sliced from the inside front corner of the heel that was originally designed to keep the wearer’s trouser hem from catching on the heel in the course of raising and lowering his legs while walking. This would really only happen with very wide legged pant more common during the Golden Age of menswear, so it’s really a vestige of the past than something with an actual purpose now; however, it’s a nod to tradition and a sign of an attention to detail.


Shoes are described as being constructed, and true to that term, they are really built of many component parts that come together to make a coherent whole. Usually, we choose shoes based on how they look and how they fit, which are important considerations, rather than for the individual structural features. However, developing an eye for everything that goes into a shoe helps you assess the quality and workmanship.

What parts of the shoe are most important to you? Tell us in the comments.

Gentleman’s Gazette


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Payless trolls shoe snobs with fake luxury ‘Palessi’ store

How much would you pay for a pair of Payless shoes? If you attended the beleaguered retailer’s recent Santa Monica event, the number is $ 600, according to Adweek. The discount shoe chain occupied a former Armani store, called it “Palessi” and stocked it with heels, boots and sneakers onto which they slapped inflated price tags…
Fashion News, Photos, and Video | New York Post


APL Debuts The Woolmark Company-Certified Running Shoe

Los Angeles-based running shoe brand Athletic Propulsion Labs (APL) has partnered with The Woolmark Company on the first technical-knit shoe to hit the global market with the wool certification trademark.
The TechLoom Breeze Merino Wool collection is APL’s most sustainable and lightest running shoe to date, made with 80 percent Australian merino wool and knitted with APL’s patented, stretch-rebound TechLoom upper to deliver strength, greater elasticity and maximum support during performance and sports lifestyle activities. It’s the first launch in a series of long-term certified wool product collaborations between APL and The Woolmark Company.
Over two years in development, the certified Wool Rich Blend engineered knit is designed to keep its shape using filament-wrapped wool yarns to add resistance to abrasion and extend wear. The yarns are also stain- and odor-resistant, naturally regulating the temperature of feet. Utilizing the latest fully fashioned knitting technology, the shoe is knitted to its final shape, reducing the amount of fabric waste often caused by regular cut-and-sew techniques. The knitting technology also allows for seamless design features such as breathable panels. Other popular brands such as Allbirds offer wool sneakers, but APL has taken a more “luxury performance” stance in the market.
Cofounder Adam Goldston explained, “After

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Shoe Toe Shapes and Detailing Explained

The toe of a shoe is the most forward projection of your body, so it literally leads the way for the rest of you.  Therefore, it’s an important style consideration that will most likely be the design focus of your shoe purchases.

The shape and decoration of the toe of your shoes will almost certainly be noticed first. In this article, we’ll explore the various shapes and ornamentation possible on a shoe’s toe and how it can affect appearance and comfort.

Spectator Tassel Loafers

Spectator tassel loafers are sure to be noticed

The Shape of a Shoe Begins with the Last

The overall shape of a shoe is created by the last, which is the name for the form traditionally made of wood and hand-carved by the shoemaker. These days lasts are also machine-made or 3D-printed from plastic.

refined lasts

Wooden carved shoe lasts

The last then serves as the mold for the upper of the shoe, thus giving it shape. The leather is stretched on the form and allowed to sit there for some time (often several weeks) until the shoe upper holds its desired shape. Shoemakers will name or number their lasts to distinguish them for themselves and their customers. The shape of the last determines the fit and shape of the shoe as a whole, and these are most influenced by the shape of the toe.

Awaiting lasting

Shoes awaiting lasts

Classic Shoe Toe Shapes

Although there are numerous subtle variations in toe shape, these can be boiled down to a handful of basic shapes, namely round, almond, square, and pointed.

Round Toes

The most basic and traditional shoe shape is the rounded toe. This can be quite spacious and therefore very comfortable, especially if you have broad or wide feet. Because the shape is simple, it tends to be innocuous on most shoes–nothing offensive but perhaps nothing exciting either.

Tricker's Stow Boot - The ideal fall companion

This Tricker’s Stow Boot is chunkier and therefore well suited to a round toe shape

Despite being basic, a truly round toe tends to look best on more structured and heavier shoes, from boots to chunky country derbies (Tricker’s, Church’s, Grenson) to trainers or sneakers, but on loafers, which already are smaller and closer fitting than other kinds of shoe, a round toe can make your feet appear shorter.

Round-toed Shoes

Round-toed loafers can make your feet look smaller

This is because the half-circle shape of the toe does not elongate the foot visually but gives it a snubbed appearance. To compensate for this the added mass or bulk of a heavier shoe is necessary. You can see this on the variant of a round-toe shoe called the Budapester, named for its origins in the Hungarian shoemaking tradition. True Budapesters have a spacious toe box with some height to it. You can see the real deal at Vass Shoes from Hungary, but versions of it can be found at Crockett & Jones and elsewhere.

Budapester shoes

The shortness of a round toe looks best on boots and chunky shoes like these three budapesters because their mass counterbalances the shortness of the toe.

Shoes that you might consider oval at the toe also fall under the “round” umbrella in many cases. These are found on traditional British dress shoes, particularly oxfords. The shape is classic and not showy.

Crockett and Jones Connaught black oxfords

Crockett and Jones Connaught black oxfords on the round-toe 236 last

Almond Toes

An almond toe is essentially a more elongated version of a round toe, shaped like the narrower end of the nut it is named after. You can think of it as a tapered oval. In my view, the almond is more flattering and elegant than the simple round toe. It’s also more contemporary with an edge of dandy style. You might say that an almond toe exists in the “Goldilocks Zone” of footwear: among toe shapes, it’s just right. It provides a bit of foot elongation but is not at all extreme. In some more exaggerated versions, you can really identify the almond shape by the way the shoe widens considerably at the ball of the foot (the base of the toes).

Almond-toe monk strap from Ace Marks

Almond-toe shoes, like these monk straps from Ace Marks have an elegant shape

Some almond-shaped toes can be chiseled. This means that instead of having a smooth curved edge along the outside of the toe, you have straight cuts or angled sides. This is most apparent if you direct your eyes to the sides or bottom of the sole since the softness of the upper can make it less obvious. A good example of the chiseled almond toe comes from British bespoke shoemaker Gaziano & Girling who are renowned for it. The shape isn’t really possible with round toes, so chiseling really begins with the longer almond shape.

Gaziano & Girling's signature chiseled toe

Gaziano & Girling’s signature chiseled toe, evident in its three angled edges

Square Toes

The general rule is to avoid wearing true square-toe shoes. This sort of toe is usually found on inexpensive footwear, and, frankly, it can be described as blunt and ugly. You’ll know these snub-nosed shoes when you see them because they are hideous and cheap looking.

square toed shoe

Ugly square-toed shoes

However, note that certain brands can call a chiseled toe a square toe. This will usually be an almond toe with a leading edge that is rather straight across the front. Crockett and Jones Square Toes

Crockett & Jones Last 348 (square toe) and 337 (called “a soft square”)One example is Crockett & Jones’ Last No. 348, which is worn by James Bond in the SPECTRE and Skyfall films and is the most widely used shape in their collection. The company calls this a square-toe, but no one would mistake it for the square toe shoe shown above.

We could call it a chiseled toe or straight toe instead, as there is no standard naming requirement across different brands. So use your judgment and trust your eyes when assessing a shoe labeled as having a square toe.

Pointed or Elongated Toes

Pointed shoes were once the rage in 15th-century Europe where they were called either crackows or poulaines.

Crackow shoes

Pointed-toe crakow or poulaine shoes were the rage circa 1470

These went to ridiculous extremes of length as a sign of virility (longer feet suggesting larger genitalia) and some even had bells at the tips.


Winklepickers were extreme to say the least

They made a comeback in the winklepickers of the 1950s British rock scene and survive today in similar rock-n-roll boots (envision alligator skin) and in some cowboy boots. Thankfully, truly pointed shoes are hard to find in dress shoes that can be worn with classic menswear.

Olive green shoes with navy trousers

Olive green shoes with an elongated last

So, rather than speaking of pointed toes, when it comes to dress shoes, it’s more useful to speak of elongation. We already mentioned that almond-toe shoes as elongated, meaning the toe area of the shoe is extended. Shoes that are not elongated normally have a small amount of space beyond where your toes end, but elongated ones have more. Bestetti elongated toe

A highly elongated last (with a round toe): Riccardo Freccia Bestetti’s Boston shoeThis is especially true of toes that are chiseled or otherwise narrowed at the front; obviously, you can’t cram your toes into an area that is tapered, so the shoe has to be longer to accommodate the shape of the last.

Crockett and Jones 348Last

Crockett and Jones 348Last

A good example of this is Crockett & Jones’s 348 last, called the “Lowndes.” As they say, “The wearer may have at least an inch of space at the front of the toe box, which will not affect the heel to ball fitting as it is more for aesthetics.”

The elongation of the Lowndes is quite subtle, but, according to Donika at Crockett and Jones’ flagship shop on Jermyn Street, many men become alarmed when they put on one of their elongated models and look down at their feet. She recommends looking at elongated shoes in the mirror, rather than just by looking down at your feet in order to gauge whether the proportions are right.

If you have smaller feet or just like the style of a longer shoe, give it a try, but, as always, moderation is the key. You don’t want to look like you are wearing oversized clown shoes, but high-quality shoes from well-established brands won’t go to extremes, so you’ll be safe with them.

Shoe Toe Decorations

Reddish Brown Captoe Double Monks

Reddish Brown Captoe Double Monks

The All-Purpose Captoe

Besides its actual shape, the toe of a shoe also contributes to the overall appearance of footwear through its ornamentation or lack thereof. The simplest toe is completely unadorned, followed by the cap toe, in which the toe area of the shoe is separated off by a line of straight stitching, shown side by side in the Crockett & Jones 337 and 348 last images above. Since simplicity of design makes an article of menswear more formal, a plain or cap toe oxford is suitable for the requirements of morning dress and black tie, as well as for business suits.

Smart Casual Details: Wingtips and Broguing

Meermin Austerity Brogue - Made in China with red lining at a high quality standard

Meermin Austerity Brogue – Note the simplicity of the stitching that forms the “wing” on the toe

Next up in terms of increasing ornamentation is the austerity brogue, which is the simplest form of wing-tip. This is made up of stitching in the shape of a W (technically, “a backward-extending point and curving sides”) to separate the toe from the rest of the shoe. The name originates from the austerity measures imposed on British shoemakers during World War II. Since they weren’t able to use the same amount of leather as required by a regular brogue, they simplified the design.

wingtip spectator derby shoes with Mid Brown Socks with Green and Cream Clocks by fort belvedere with brown trousers

A spectator wingtip clearly shows the detailed design of the toe box in the usual wingtip, the wing shape is made up of a pattern of perforations that resembles lacework, but you can also find this as a straight band forming a captoe. This is the broguing, which was originally designed to allow water to drain out in country shoes worn in wet, muddy conditions.

Wingtip Cognac Antique

Wingtip in an antiqued cognac leather

The Formal Medallion

The last sort of broguing related to shoe toes is the medallion. This is an ornate geometric or floral pattern of perforations adorning the toe cap. You can find these alongside other brogue details, but they are sometimes the only bit of ornamentation on an otherwise fairly plain shoe. The latter will not be as formal as a plain cap toe, but a medallion can still feature on oxford shoes.

Beautiful Medallion with 12 hole lacing

Beautiful Medallion with 12 hole lacing

The Laid-Back Split Toe

Back to more casual shoes, there is one other type of toe feature that is worth mentioning, and that is the famous Norwegian split-toe, found on lace-up derbies and, occasionally, penny loafers. As the name says, there is a vertical seam right in the middle of the toe. Because of the visible heavy stitching, these shoes tend toward the casual, to be worn as any other derby.

suit slacks in mid-brown with split toe derbys

A pair of vintage Norwegian-toed derbies made by Mannina of Florence with a split toe

Toe Color Variations

Finally, it’s worth mentioning that shoes can also feature a toe in a different color or material than the rest of the upper, such as cream suede on the vamp and brown calf leather at the toe. These are spectators, whether captoes or wingtips. But, for those who find spectators too showy and want a more subtle difference, many a brown dress shoe is available off the shelf with color variation in the patina, usually darker tones of brown, at the tip.

Half Brogue without Medallion & two tone Ghillie brogue shoe by Ugolini

Two-tone Ghillie brogue shoe by Ugolini at right


Like other style details–shirt collar shape, the rise on a pair of pants, or lapel width on a suit–the choice of toe shape should be governed by what looks best with your physical features. Just as a man with a round face should not wear a wide-spread shirt collar because it increases the impression of width, if you have smaller feet, you should probably avoid rounded toes and try an elongated last. The choice can balance your proportions.

It is also important to realize that these toe shapes also often appear in combinations, so you might have a shoe that is elongated with chiseled sides and a square toe, but once you know the varieties you should be able to identify them when you examine a pair of shoes. Then choose the shape and amount of ornamentation that suits your personality best.

Gentleman’s Gazette


Look like a Gentleman, Travel in Style and Enjoy the Best in Men’s Accessories at Hook & Albert. Get 20% Off Your First Order with Coupon Code TAKE20. Shop Now!

New Adidas Shoe Line Made From Recycled Ocean Plastic

Adidas has come out with a shoe line that has ocean activists captivated.

Adidas paired up with Parley for the Oceans to create an eco-friendly shoe line made from recycled ocean plastics.

A message from Parley for the Oceans: 

Here are the problems our ocean is currently facing. A massive amount of plastic trash ends up in our oceans every year. The ocean currents have formed five gigantic, slow-moving whirlpools where the plastic collects, nicknamed Vortex. Recent studies indicate that at least 5 trillion pieces weighing over 250,000 tons are now floating in the world’s oceans. The majority of the plastic debris sinks or remains in the Vortexes, however, a significant percentage of it washes onto our coastlines daily.

After sunlight photodegrades the plastic into small pieces, aquatic life and seabirds mistake these fragments for food and ingest it.

While it’s difficult to know exact figures, a 2012 report from WSPA indicates that between 57,000 and 135,000 whales are entangled by plastic marine debris every year in addition to the inestimable – but likely millions – of birds, turtles, fish and other species affected by plastic marine debris.

New studies show that ingested plastic damages the internal organs of fish. This raises the question about the safety of our seafood.

Turtle and Plastic in the Ocean
Underwater image of a turtle with plastic on his head.


In this day and age, human consumption and pollution are at an all-time high. The Straw Free Campaign by the National Parks Services confirmed that on average American’s use over 500 million straws per day. We know how detrimental plastics, if not disposed of correctly, can majorly affect our world.

That’s why the internet broke when the Adidas brand recognized the heavily discussed social issue and came up with an efficient way to get involved without compromising their reputable brand.

Everything Adidas does is rooted in sport and technology. The responsive running shoes made entirely from ocean plastic are described as following:

These women’s running shoes are created with yarn made in collaboration with Parley for the Oceans. They have an Adidas Primeknit upper built with yarn spun from Parley Ocean Plastic™. The Boost midsole absorbs the force from your footstrike to release it at push off for a super-charged ride. The women’s-specific design offers adaptive support, comfort, and stability. Wet or dry conditions, a grippy outsole delivers sure-footed traction.

New Adidas Shoe Line Made From Recycled Ocean Plastic
New Adidas Shoe Line Made From Recycled Ocean Plastic

“By 2020, Adidas wants all of their shoes to be made using recycled plastic, which is good for the health of the planet, but it’s good to know that their first foray into sustainability has been a success”. – Business Insider

So if you’re looking for a brand that provides technologically innovative and quality products, as well as a positive environmental impact, consider Adidas!

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