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Gentleman’s Guide to Dress Shoes

When it comes to casual footwear, then it’s more or less clear what to wear with different types of clothing. After all casual wear is casual, and it allows for more experimentation and irregularity.
Things are more strict when it comes to formal wear and hence why it’s called the dress code. When you visit T.Clark Shoes, we will be delighted to share this knowledge with you in depth. In a meantime, we have written the guide below to help you get started.



This name is solely referred to the shoes with a “closed lacing” featuring shoelace eyelets tabs that are attached under the vamp. Oxford’s usually a preferred choice for the formal style of shoes. Fitting of those must be done precisely to your foot as there will be little giving during the wear if fitted improperly.
Oxford-1  Oxford-2  Oxford-3  Oxford-4


This style is solely referred to the “open lacing” eyelet tabs that are stitched directly to the vamp. This type of construction is often used on less formal shoes for a more relaxed appearance and added comfort.
Derby-4  Derby-2  Derby-3  Derby-1


Wholecut shoes are made from a single piece of leather usually having only one stitching line behind the heel. This style of shoes is done with a minimalistic approach and can be worn for formal or dress purpose displaying pure elegance through their narrow shape, clean lines and smooth surface.
Wholecut-1  Wholecut-2  Wholecut-3


This style has no lacing and is fastened by one or two buckles, more rarely three. Monk Straps considered being less formal than the Oxfords, but dressier than the Derbies. In the modern day fashion, two strap Monks are the most popular style.
Monks-1  Monks-2  Monks-3  Monks-4


Referred to all slip on shoes that have no lacing. Traditionally loafers are designed to be less formal and more casual footwear; however some styles that are made from high gloss leather of a plain nature can be worn for a very formal purpose. Other loafers that have elements of formal styles (such as Toe Cap, Brogue, Bike Toe, etc.) can also be used as a dress or business shoes.
Loafer-1  Loafer-2  Loafer-3  Loafer-4



Though not as tough as the Toe Cap style Plain Toe considered to be more versatile shoes showing masculine look construction for a business purpose while retaining its formal simplicity.
Plain Toe shoe style is trusted to be the most adaptive and practical out of all other styles though in some opinion lacking character.
Plain-1  Plain-2  Plain-3  Plain-4


The toe area of this style is reinforced with extra thick leather cap allowing this shoe to retain its shape even after many years of use. Due to their versatility, formal look and strong manly construction the Toe Cap shoes are the preferred choices for business wear though often worn for formal occasions when made from high shine or pattern leather. The versatility of this style also allows it to be worn for casual dress purpose on par with brogues when made from soft calf leather of various colours.
ToeCap-1  ToeCap-2  ToeCap-3  ToeCap-4


Originated from Ireland and Scotland the Brogue shoes showing a real taste of character and true versatility. These shoes can be worn for business, dress or even casual purpose. Though more affected by fashion than the other styles brogues have always been part of men’s wardrobe from the early days.
Brogue-1  Brogue-2  Brogue-3  Brogue-4


This style of shoes is usually referred to square or chisel toe shape form of various width and the upper of the shoes featuring two seam lines running from the top of the shoe to the toe. This style is mainly worn as a dress or casual dress and less as formal footwear.
BikeToe-1  BikeToe-2  BikeToe-3  BikeToe-4


In 1930’s traditionally pain loafers were first made with a single strap for a decorative purpose which was soon used to hold polished pennies to enhance the appearance of the shoes further. That is how the name Penny Loafer was born and lasted until today. This is a smart casual traditional style that goes equally well with a dress or casual outfits when more layback character is required.
PennyLoafer-1  PennyLoafer-2  PennyLoafer-3  PennyLoafer-4


As opposed to Penny Loafer the Bits featuring a shiny metal bar that looks like a Horsebit from the horse tack used in equestrian activities. Though considered a very classic old school style first introduced by Gucci in mid-60’s, Bit Loafers are slowly coming back to fashion again.
BitLoafer-1  BitLoafer-2  BitLoafer-3


A casual dress style of loafer that has two decorative tassels on the upper of the shoe. It started off in 50’s as basic casual footwear, but similar to brogues tassel loafers were gradually accepted as a dress shoe. Tassel Loafers also come in variation as Kiltie Loafer for more casual look.
Tassel-1  Tassel-3  Tassel-2



Slip on boots that have elasticated gussets on each side and a holding loop on a back of the shoe to assist in putting them on. Showing true versatility they can be worn as a dress or smart casual and are a good choice for various outfits. Chelsea Boots are strongly associated with Beatles who were wearing them in mid 60’s during their visit to New Zealand, which instantly won them the popularity.
Chelsea-1  Chelsea-2  Chelsea-3  Chelsea-4


This style of ankle boots is fastened by Derby type lacing that usually have only two to four eyelets. They are considered to be less formal than Chelsea or zip boots, but some styles that are made quite plain can be worn for dress purpose. Chukka is a Low Ankle style and is the preferred choice for dress and casual style of boots while Full Ankle lace up boots is generally of a more casual appearance.
Chukka-1   Chukka-2  Chukka-3  Chukka-4


The Zipper Boots considered being the most formal style out of all other boot types due to their plain appearance and simplicity.