Recommendation Report: An Introduction
to Men’s Dress Shoes.
To: The reader, the new gentleman wanting to invest in dress shoes
Writer: Kien Yee, student at ACC
Recommendation Report: Men’s Dress Shoes
The purpose of this report is to analyze dress shoes. This report will examine the various styles dress
shoes come in, the purpose of each style, different types of shoe construction, and finally, this report will
recommend what dress shoe should be your first purchase. This report is for the gentleman who wishes to
refresh his wardrobe and is wondering where to start when it comes to dress shoes.
Why do I need a Dress Shoe?
Despite what you may have been told, looks do matter. It might not be fair because we all know that there
is so much more to a person than what they look like, but the fact remains: looks matter. Appearance has a
big impact on how we treat and perceive others, and it even affects how we treat and perceive ourselves.
For example, a fresh haircut will have you feeling more confident, happier, and good. On the other hand,
a bad hair day can completely ruin your mood. Another aspect of appearance, besides hair, is how we
dress; and what we put on our feet can completely make or break an outfit. Would you wear your running
shoes with a 3-piece suit? Hopefully not, because that would ruin the entire look. Instead, you would opt
for a pair of dress shoes.
Points of Examination
There are many options to choose from when it comes to dress shoes. This report will organize these
options into the following categories.
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Dress shoe styles: Dress shoes come in different styles such as the oxford, derby, penny loafer,
tassel loafer, double monkstrap, singlemonk strap, and others.
Purpose of each style: Not all dress shoes serve the same purpose. Some serve more formal looks,
and some, more causal looks.
Dress shoe construction: Dress shoes involve various parts and layers in their construction, and
not all dress shoes are created using the same method.
Men’s Dress Shoe Styles
There are many different men’s dress shoe styles. Men’s dress shoes are generally made from leather, and
we will look at 3 main categories: Lace- ups, Loafers, and Monkstraps. This report will examine styles
from each category, starting with the Lace-ups, moving to the Loafers, and lastly the Monkstraps.
The Lace-Ups
There are two main types of lace-up dress shoes: Oxfords and Derbys.
Oxfords: When it comes to dress shoes, oxfords are likely the first style that comes to mind. And for good
reason too. They are a classic men’s wardrobe staple that looks stylish, professional, and simple. Oxfords
are characterized by its utilization of shoe laces in a closed lacing system and by how the eyelet flaps
and tongue are sewn under the vamp. They come in different colors. The most common and traditional
colors are brown and black. Browns can range from a light tan to a deep dark coffee brown.
Oxfords can come in “plain toe”, “cap toe”, “wingtip” and “whole cut”, where the upper of the shoe is
made from one piece of leather, making for a smooth and seamless design. In the picture below and left is
a brown, smooth leather, cap toe oxford, which is a classic look.
Oxfords can also have broguing, which is a pattern of small variously sized holes that serve as a
decorative element. Broguing can be seen on plain toe and cap toe oxfords, but it is most seen on wingtip
oxfords, as shown in the picture below and right.
Derbys: Derbys look similar to oxfords, and they can sometimes be confused with each other; but they are
different, and the differences are subtle. Derbys are less form fitting than oxfords, having a wider, roomier
profile. The biggest difference is the eyelet flaps. They are sewn on top of the vamp, as opposed to under
the vamp as it is with oxfords. The tongue and the vamp are one piece, and the shoe laces are used in what
is called an open lacing system. The picture below shows the difference between derbys and oxfords. On
top is an oxford and below that is a derby.
Derbys can have broguing and come in as many different colors as oxfords. Like oxfords, there are plain
toe and cap toe derbys, as well as wingtip derbys. Despite their similarities, the subtle differences make
the derby less formal than the oxford.
The Loafers
Loafers are a versatile classic and belong in any man’s wardrobe.
They come in many forms, such as penny loafers, tassel loafers,
and bit loafers. Loafers feature a lace-less, slip-on design and a
characteristic top stitching that starts at the strap and comes
around the toe. They are made in various colors with the most
common being black or brown, ranging from light to dark. They
can be made from smooth leather or the more casual option,
suede.
Penny Loafers: Penny loafers are the most versatile. Penny loafers feature a strap sewn across the top of
the vamp. As seen in the picture on the right, the strap has a slit that can fit a penny, hence the name,
penny loafer.
Tassel Loafers: Tassel loafers follow all the hallmarks of a loafer design including a strap sewn across the
top of the vamp. Instead of a slit, these loafers have tassels, which serve a decorative purpose.
Bit Loafers: Bit loafers are another classic. Across the strap, spans a metal buckle called a horsebit. Like
tassels, the bit is a decorative element.
The Monkstraps
Another classic option is the monkstrap. Monkstraps feature a low-cut fit and a wide tongue with a strap
laid across it and secured with a saddle buckle on the outside, giving the monkstrap its signature look.
Monkstraps are traditionally made from leather, and brown and black, as with all dress shoes, are the most
common colors. Monkstraps come in a variety of designs, with the most prominent differences being
found in the strap and buckle. Straps can differ in length, width, angle, cut-outs, and spacing. Buckles can
differ in design, shape, size, color, and material. However, they can be categorized into two main types,
single monkstraps and double monkstraps. Triple monkstraps exist but are not common as it makes the
shoe look too busy and oversaturated.
Single Monkstraps: Single monkstraps are the more traditional design and it features a single strap and
buckle; no need for laces here.
Double Monkstraps: Double monkstraps are just that, monkstraps with double straps and buckles.
Spacing and angle between the straps, along with buckle placement, are the main factors that influence
the aesthetic of the shoe.
Purpose of the Styles
The shoe is an integral part of an outfit. It is not an accessory that can be left out, so that makes choosing
the right shoe top priority. A shoe must complement the clothing. Therefore, the shoe you select depends
on the features of your clothing, like the color and style of your shirt and pants or the material of your belt
and watch. Depending on the occasion, your dress will be more formal or casual, and you will select your
shoes accordingly. We will go through the different styles and analyze their levels of formality and
versatility.
In terms of color and material, formality is measured the same across all the styles mentioned. Regarding
color, black is the most formal. Browns range from light tan to dark as black coffee, and the darker it is,
the more formal it is. Regarding material, smooth leather is more formal than suede. See the formality
chart for reference.
Lace-ups: Lace-ups are the most formal of the shoes mentioned in this report. They come in more
casual forms too which make this an extremely versatile style. Type, material, and color all affect
formality. Regarding type, oxfords are more formal than derbys.
Shoes complement the clothing. For a black-tie event, a black, smooth leather, plain or cap toe oxford is a
must. For a dark colored formal suit, wear a black or dark brown, smooth leather, cap toe oxford or derby.
As we move into the business and smart casual dress code, we have more options. Broguing and wingtips
are on the table. Medium to light browns in smooth leather or suede can be worn. A black lace-up does
not generally work with business or smart casual, unless wearing black or dark colors. However, dark
browns work better with this dress code, making it a versatile color.
Loafers: Loafers complement a range of dress codes, from business casual to smart casual to casual.
They can even be worn with casual shorts. This makes them very versatile. The type of loafer, whether it
be penny, tassel, or bit, does not significantly affect formality.
A black or dark brown smooth leather loafer will be the most formal option, so wear them with your most
formal business casual outfits. As we get more casual, we can explore medium to light browns and suede.
However, black and dark brown are not off the table even in casual styles if you are mindful of the style
and color of your clothing.
In terms of versatility, the penny loafer tops the tassel and bit loafer. Because the design is sleeker and
simpler, the penny loafer pairs with simpler outfits just as well as with more elaborate ones. The tassel
and horsebit are decorative elements and pair better with outfits with more stylish elements. This makes
the tassel and bit loafer less versatile. The least versatile is the bit loafer. Generally, your metals should
match, so you would need to factor in the color of the horsebit, your watch, and your belt buckle.
Monkstraps: Monkstraps complement outfits in the business casual and smart casual dress code, making
monkstraps the least versatile. Single and double monkstraps are on the same level of formality.
Wear black or brown leather monkstraps, single or double, with your business casual suits. As we get
more casual, we can wear lighter brown and suede monkstraps. Single and double monkstraps are equally
versatile. A brown leather monkstrap would prove the most versatile. Remember the buckles are
metal, and a fashion rule of thumb is to match your metals, like your watch and belt buckle.
Construction
There are different methods to construct dress shoes. The three that this report will look at are: a
Goodyear welt, a blake stitch, and a cement construction.
Goodyear Welt: Goodyear welt construction involves two sets of stitching and a welt, which is a strip of
leather or rubber that goes around the rim of the shoe. The welt is sewn into the upper and the insole and
this is the first set of stitching. Lastly, the welt is sown into the midsole and the outsole. This construction
proves to be the most durable and waterproof, because the welt acts as a barrier; but also, the most
expensive.
Blake stitch: A blake stitch construction does not require a welt and generally uses one set of stitching.
The upper and insole are sewn directly to the mid and outsole. This provides for a sleeker appearance and
is simpler and cheaper. However, it is not as durable or waterproof as a goodyear welt.
Cement: Cement construction is the most common type found in shoes today. It uses an adhesive to glue
all the layers together and it requires no stitching, although you may find faux stitching on some shoes
that use this method. This simplicity allows cement construction to be the cheapest, but also the least
durable and least waterproof.
Conclusion
Ideally, your shoe collection would include at least one pair from each style for increased flexibility. For
events with a strict dress code, like Black Tie, a black leather plain or cap toe oxford is a requirement. For
less formal settings, a black leather oxford may not work, and you would need a different color or a
different style altogether. However, buying multiple shoes would have a big upfront cost, so increasing
your collection slowly as finances allow would be your best strategy.
Recommendation: Any shoe collection starts with one pair, and I suggest the best shoe to start with is
a medium, dark brown leather oxford with a goodyear welt construction. Start with a plain toe or go
with a cap toe for some added interest; it is up to you.
Although relatively plain and simple, a brown leather oxford is extremely versatile. Able to be worn with
many dress codes, the brown leather oxford completes formal looks and enhances smart casual looks.
A brown leather oxford is standard with those business suits, and while simple, it adds a level of
sophistication to those smart casual outfits. It is always better to be overdressed than to be underdressed.
I suggest a goodyear welt construction because it is the most durable. It may cost more than other
methods of construction, putting you around $200 or more for a quality pair, but it will last a lot longer.
When the sole finally needs to be replaced from years of wear, the goodyear welt construction method
allows the shoe the ability to be re-soled, so you can wear it for even longer.
Wear your shoes often. When quality genuine leather shoes show signs of wear and usage marks, it gives
them character and personality, as well as style points. Clean, condition, and polish them periodically and
they will last a long time.
Works Cited
Boardroom Socks. “Men's Loafers: The Ultimate Guide to Buying & Styling Loafers.” Boardroom Socks,
boardroomsocks.com/blogs/dress-sock-blog/mens-loafers.
Collins, Jack, et al. “Oxford Shoes Guide - Wearing, Buying, & What to Avoid.” Gentleman's Gazette, 18
Nov. 2019, www.gentlemansgazette.com/oxford-shoes-guide/#style-guide.
“The Difference between Oxford and Derby Shoes.” Beckett Simonon,
www.beckettsimonon.com/blogs/resources/the-difference-between-oxford-and-derby-shoes.
“Goodyear Welt Construction: Why It Matters.” Thursday Boot Company,
thursdayboots.com/pages/goodyear-welt-construction-guide.
Ingevaldsson, Jesper. “History - the Blake Construction.” Shoegazing.com, 17 Jan. 2022,
shoegazing.com/2022/01/16/history-the-blake-construction/.
Schneider, Sven Raphael, et al. “Monk Strap Shoes & Double Monks Guide.” Gentleman's Gazette, 8
Nov. 2018, www.gentlemansgazette.com/monk-strap-shoes-guide/.
Schneider, Sven Raphael, et al. “The Derby Shoe & Blucher Guide.” Gentleman's Gazette, 13 June 2018,
www.gentlemansgazette.com/derby-shoe-blucher-guide/.
Theo Rosen·Men's Style·April 12, 2022, et al. “How to Wear Loafers for Men; Casual to Formal Attire.”
Albert Review, 14 Apr. 2023, albertreview.com.au/style/how-to-style-loafers/.