The Ultimate Men’s Dress Shoe Guide

The anatomy and style of
classic men’s dress shoes.

Written by Jacob Sigala [All images and graphics by Creative Studio]
Having a superb pair of dress
shoes is not a luxury; it’s a necessity. Even sneaker and hoodie guys will
occasionally need to suit-up, and opportunity favors the prepared.
This guide will help you make
wiser shoe purchasing decisions. Once you understand the available options,
you’re already halfway there toward looking your best at any event.

Deconstructing the Dress Shoe

vamp, upper, sole, quarters, facing, toe, heel
Before we get down to nuances
in style, you should first understand the components that make up a dress shoe.
From front to back, a dress
shoe consists of four parts: toe, vamp, facing, and quarter. It’s the placement
and construction of these four pieces that determine the individuality of a
dress shoe.

The Oxford

The Ultimate Guide to Dress Shoes: Oxford Balmoral
Oxfords, the most basic and
timeless of dress shoes, are an excellent starting point. The versatile Oxford
shoe can be dressed up or down for formal and daily wear.

A Little History

These shoes gained popularity
in 1800 among college students, particularly at Oxford University. At the
century’s turn, students wanted a modern low-top version of the shoe, as they
deemed the half-boot style of traditional Oxonian shoes outdated.

How to Identify

The most recognizable trait of
an Oxford shoe is its “closed lacing”; this means that the shoe’s facing is
attached beneath its vamp. This arrangement provides a slim silhouette that
hugs the foot’s contour.
dress shoe guide oxford shoe

How to Wear

Oxfords are chiefly popular
because of their minimalism and their ability to pair with any outfit.

  • For everyday wear, there’s a
    wide range of colors from brown to blue to dark red to green, in both leather
    and suede.
  • For business attire, dark
    brown, cordovan, English tan, and black leather are your safest choices.
  • If you’ll be pairing Oxfords
    with a tuxedo or other formal wear, black patent leather is your best bet.

The One Piece Oxford

The one-piece Oxford is a
variation on the classic oxford. It’s constructed of a single leather piece
rather than various pieces sewn together, and it has a single seam. This
limited stitching provides a sleek and sophisticated look that adds to the
shoe’s simple, no-nonsense style.
The Derby

The Ultimate Guide to Dress Shoes: Derby, Blucher
The Derby is similar to the
Oxford, but it’s a more casual dress show.

A Little History

The Derby shoe, also known as
the Gibson or the blucher, was a sporting and hunting boot circa the 1850s. At
the turn of the 20th century, they became appropriate for going out into town.

How to Identify

Derbies are often
miscategorized as Oxfords since their shapes are very similar and their
differences are very subtle. The key difference between Derbys and Oxfords is
that the Derby shoe has its facing attached on top of the vamp. This is called
“open lacing” and allows for a wider fit.
This wider, comfortable fit
winks at the Derby’s sporting roots and solidifies the Derby shoe’s positioning
as more casual than the Oxford.
dress shoe guide derby shoe

How to Wear

You can wear and style Derby
shoes the way you would Oxfords. However, Derbys are typically more casual, so
you wouldn’t want to wear them with a formal suit. Chinos and rolled jeans,
however, would go pair with these shoes.

The Monk Strap

The Ultimate Guide to Dress Shoes: Monk Strap
A laceless shoe that is more
formal than the Derby but less formal than an Oxford.

A Little History

This shoe takes its name from
the monks who originally donned them, as this simple closed-toe design provided
greater protection than their traditional sandals.

How to Identify

A Monk Strap is similar in
shape and construction to an Oxford, but instead of an eyelet closure, it has a
wide swath of leather fastened across the front of the shoe. This wide strap is
fastened with either a single or double-buckle closure.
dress shoe guide monk strap shoes

How to Wear

This classic alternative to
laced dress shoes adds a certain panache to any outfit.

  • The monk strap is now regarded
    as a very versatile shoe that can be worn with cuffed jeans or the most dapper
    of suits.
  • Monk straps attract 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 have decorative brogueing.

The Loafer

The Ultimate Guide to Dress Shoes: Loafer
The loafer is a
moccasin-inspired shoe that is known for its slip-on style.

A Little History

The original loafer was a
casual house slipper made for King George VI of England. It was neither
acknowledged nor popular as a casual shoe until it came to the U.S. in the
1930s. It wasn’t until the 1960s that American businessmen and lawyers began
wearing loafers with suits.
In 1966, Gucci introduced the
bit loafer, which 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.

How to Identify

Loafers often have a saddle —
a decoration that might be a plain strap, a strap with a slit (as with penny
loafers), or a metal ornament. Tassels or a kiltie might hang from a saddle,
while the minimalist loafer (the Venetian) has an exposed vamp without
embellishment or ornamentation.
A signature characteristic of
loafers (especially those more akin to a moccasin than a regal slipper) is an
elevated seam that runs along the toe.
A casual variant of the loafer
is the driving moccasin or driving shoe. These are often made of softer
materials, are less structured, and have soles and heels made for
wearer-comfort while driving.
dress shoe guide loafers
How to Wear

Wear clean Venetian loafers or
embellished loafers with suits for formal settings. You can also opt for casual
styles with rolled jeans.

The Dress Boot

The Ultimate Guide to Dress Shoes: Dress Boot
The dress boot is a short
lace-up boot. It is constructed like an Oxford, but with a longer shaft.

A Little History
This shoe style’s roots from
the Victorian era, when men had limited footwear options. The dress boot
quickly became an acceptable choice for formal daywear, and it still remains an
attractive alternative to standard dress shoes today.

How to Identify

A dress boot is constructed
like an oxford, and is very often the same shape but with a longer shaft. This
short, lace-up boot may feature wingtip brogueing on the toe and along its
dress shoe guide dress boots

How to Wear

When is a boot dressy enough
to be worn with a suit?  It should be
sleek, not too chunky, have thinner laces, and its soles should immediately
distinguish the boot as a high-top dress shoe. Lug soles and commando soles
will rarely be appropriate (though there are exceptions.)

  • If the boots are made of fine
    leather, they can be brown or black or almost any other, so long as they
    complement the suit.
  • Unless you are a styling
    expert, assume that a suede dress boot is a contradiction (though it need not

The Chelsea Boot

The Ultimate Guide to Dress Shoes: Chelsea Boot
The Chelsea boot is a
versatile laceless ankle boot.

A Little History

The Chelsea boot originates
from Victorian England, reputedly created by the Queen’s bootmaker, J.
Sparkes-Hall. These boots became the practical alternative to rigid Victorian
boots of the age and were quickly adopted by equestrians.
Chelsea boots experienced a
strong, permanent revival in the 1960s when The Beatles wore them as part of
the British Mod look.

How to Identify

These ankle length boots have
rounded toes, low heels, and elastic gussets on the sides. Because of these
elastic gussets, one can pull on and slip off the shoes with ease, without
compromising the refined silhouette of a laced boot. In fact, the absence of
laces contributed to the Chelsea’s slim, clean shape.
In dressier versions, the vamp
and quarters are made from a single piece of leather, which keeps stitching to
a minimum for a tidy look.

How to Wear

Classic Chelsea boots don’t
have decorative flourishes or embellishments. Their simplicity puts them in a
class all their own: jeans get an upward lift, and traditional suits gain an
edge.  If you purchase suede Chelsea
boots, wear them only as part of a casual or smart-casual ensemble.
The Chukka Boot

The Ultimate Guide to Dress Shoes: Chukka Boot
A lace-up boot with only two
to three eyelets on each side.

A Little History

Chukka boots originate from
the polo sport: a “chukka,” a segment of seven minutes, is the unit of time by
which polo matches are measured; a match will consist of four, six, or eight
Some say chukkas resemble
shorter versions of the boots worn by polo players. People also say that
Chukkas are intended to be comfortable after-game footwear for polo
players–like the original Uggs were for surfers.

How to Identify

Chukkas are ankle-length boots
with few eyelets. The absence of many eyelets and the short shaft allow for a
snug fit that won’t disrupt the shape of one’s trouser legs. Also, Chukkas have
a rounded toe, minimal stitching, and open lacing (similar to the derby). They
are traditionally made of soft suede, but there are now many versions from
which to choose.

Desert boots are a much more
casual, rubber-soled version of the Chukka boot.

How to Wear

These are the most casual
shoes we’ll discuss in this article. Chukkas are not appropriate for formal
attire, though pairs made of high-quality leather can complement a smart-casual
ensemble. Both chukkas and desert boots are exceptional for smart-casual.

The Opera Pump

The Ultimate Guide to Dress Shoes: Opera Pump
The most formal of dress

A Little History

Popular during the Victorian
era, opera pumps essential to formal evening wear. Men would wear these pumps
with knee-high stockings and breeches to operas, dances, and other formal

How to Identify

Opera pumps are slip-on dress
shoes. They are traditionally made of patent leather and are adorned with a
grosgrain bow.

How to Wear

Though not as popular today,
opera shoes occasionally make an appearance at full-dress events. If you’re a
fashion-conscious individual, you can wear opera pumps with a tuxedo or suit at
a ritzy soiree.

Dress Shoe Toe Styles

cap toe, wingtip, plain toe, medallion, apron, split toe
When making an investment in
quality footwear, take note of the details, and abide by the one golden rule:
the toes of your dress shoes should be rounded, and never squared or pointy.
There’s a time and place for
pointy and squared toes, but not on dress shoes.

Plain Toe

Plain toe shoes are as simple
as it gets. The vamp is unadorned, and the resulting look is clean and

Cap Toe

Cap toes feature a horizontally
stitched line across the vamp that “caps” the toe. In most cases, a separate
piece is stitched over the vamp. But sometimes, the cap is accomplished by a
decorative stitch across a single piece.

Split/Apron Toe

The split toe, otherwise known
as the apron toe, features a seam that starts at the middle of the toe, runs
around the shoe, and ends at the middle of the heel. This toe style is more
common on casual shoes.


The medallion style has a
plain toe, with hints of brogueing on top of the toe.


This toe style has a winged
cap that peaks in the middle of the toe. Wingtips often feature brogueing in
the center of the toe and along the seam of the cap.


Any dress shoe style can have
brogueing. Brogue simply refers to the decorative perforations in various
Originally, the tiny holes
were intended to allow water out of shoes when crossing wet terrain. Brogueing
is most often seen on Oxford, Derby, and Monk Strap shoes in four toe cap
styles: full brogue, longwing brogue, semi-brogue, and quarter brogue.
full brogue, semi-brogue, half brogue, quarter brogue, longwing, long wing brogue

Full Brogues / Wingtips

Also known as wingtips, the
wing-shaped cap extends around to the outside of the toes.


Semi-brogues, also known as a
half brogues, feature broguing along the seam of the cap toe as well as some
decorative broguing on the center of the cap toe. This is more subtle than a
full brogue.

Quarter Brogues

The most reserved of the lot,
the quarter brogue simply features decorative broguing along the seam of the
cap toe, with no decoration on the center of the cap toe.
Longwing Brogues

Longwing brogues are most
common on the derby shoe. The shoe’s brogued wingtip cap continues along the
side of the shoe all the way to its center seam in the back.

Take Your Pick

A signature pair of well-made
dress shoes is an essential possession. Choose a well-crafted pair, and choose
Ideally your choice expresses
your personal style and fits with the clothes you typically wear. You can add
uniqueness and dimension to them with creative lacing methods or colorful


Not everyone can spend a
fortune on dress shoes. Take into consideration how often you will be wearing
them, and where you’ll be wearing them. There’s no need to break the bank if
you’ll only wear dress shoes occasionally at weddings, funerals, etc. But if
you’ll be wearing dress shoes as part of your daily professional ensemble, we
suggest spending a bit more than you’d think to. Regular wearers who dress to
impress should spend as much as one can comfortably afford to spend. Consider a
well-made pair of dress shoes as a small investment.
The graphic below was designed
for your convenience, and we welcome you to share it.
The Ultimate Guide to Dress Shoes

Jacob Sigala

Kayode Ojo
Kayode Emmanuel Ojo is the Co-Founder and Managing Director at SHEFFA Limited. He is presently studying Computer Science at the National Open University, Victoria Island, Lagos.