Ultimate Dress Shoe Guide

A great pair of go-to dress shoes is a necessary staple for any man’s closet. Even the most casual of men will need to suit up at one point or another, and before you lump all “dress shoes” into one category,  find the right pair that suits you with our dress shoe guide. If you take the time to find a classic pair that is worth investing in, with the right care, they will truly last you a lifetime. Whether you’re a seasoned shoe aficionado, or just trying to cover your bases, we’ll break it down to the basics and make choosing the right pair simpler than you initially thought.


In order to understand a style, one must first understand the components that make up a men’s dress shoe. From front to back a dress shoe is divided into four parts: toe, vamp, facing and quarter. It is the placement or construction of these pieces that give the following dress shoes their unique style.

vamp, upper, sole, quarters, facing, toe, heel


The Oxford Shoe

The Ultimate Guide to Dress Shoes: Oxford Balmoral

The oxford is the most basic and timeless of the dress shoes, and a great starting point if you’re looking for a classic staple. They are very versatile option that can be dressed up with formal wear or down for a more casual arena. Gaining its name from its history at Oxford University, oxfords were a newer version of the popular Oxonians that were popular at the university in 1800. This half-boot style became outdated and students looked for an alternative style that was more current, thus the oxford shoe was born.

The shoe is characterized by its facing being stitched on under the vamp, or “closed lacing.” The facing’s placement provides a slim silhouette that hugs the foot’s contour. The oxford is one of the most popular styles due to its minimalist appeal and ability to go with just about everything. For general everyday wear, stick to a dark brown or black standard leather pair, while if you’ll be pairing them with a tux, a patent leather pair will fit the best.

The One Piece Oxford Shoe

This shoe is a variation on the classic oxford that is constructed of a single piece of leather rather than various pieces sewn together. This style has only one seam connecting the piece of leather together in the back of the shoe while maintaining the original Oxford shape and signature “closed lacing.” The sparse stitching gives a sleek and sophisticated look that adds to the shoe’s unique and minimalist style. Though this style is unassuming, it is a uncommon variation on the typical oxford shoe and is seen quite rarely. It can be dressed up or down depending on the type of leather and material of the sole. For example, a patent leather, leather soled version would definitely up the ante when paired with a formal suit or tux, however a full-grain leather, rubber soled version pairs nicely with chinos or dark-wash jeans. The One Piece Oxford is for the detail-oriented man that wants to make a minimalist statement.

The Derby Shoe

The Ultimate Guide to Dress Shoes: Derby, Blucher

The derby shoe, also known as the Gibson or the Blucher, were originally intended as a sporting and hunting boot in the 1850’s. At the turn of the 20th century, derbies began to be appropriate footwear to wear into town. Derbies are often miscategorized as oxfords, as their shape is very similar and their differences are very slight. Though not obvious upon first glance, the difference lies in the facing placement. The derby shoe has the facing stitched on top of the vamp as opposed to an oxford with its tabs sewn on under the vamp. This construction, called “open lacing,” allows for a wider fit than an oxford, making it a more comfortable option. This simple detail, has kept the derby reminiscent of its sporting roots and acts as a less formal version of the oxford.

The Monk Strap

The Ultimate Guide to Dress Shoes: Monk Strap

The monk strap serves as the intermediate between the oxford and the derby in terms of formality, featuring a similar shape sans the laces. In place of an eyelet closure, the monk strap has a wide strap that is fastened across the front of the shoe with either a single or double buckle closure. The monk strap takes its name from the monks who originally donned them. The closed toe design was a much more protective alternative to wear while working than the sandals they usually wore.

This alternative to traditionally laced dress shoes adds a certain panache to any outfit in need of a little something extra. The monk strap has become a very versatile shoe style that can be dressed down with some cuffed jeans, or dressed up with your most dapper of suits. This is definitely a shoe that begs for a little attention and can easily become the focal point of  an ensemble. Monk straps are often crafted out of leather or suede and can be found with and without decorative broguing.

The Loafer

The Ultimate Guide to Dress Shoes: Loafer

The loafer is a moccasin-inspired shoe that is most recognizable by its slip-on styling. The loafer was originally intended as a casual house slipper made for King George VI of England. The loafer did not become popularized as a casual shoe until the style crossed the pond and began being manufactured in the United States in the 1930’s. It kept its status as a casual-only shoe until the 1960’s when American businessmen and lawyers began wearing loafers with suits. In 1966, Gucci introduced the bit loafer featuring a metal strap across the front in the shape of a horse’s bit, further elevating the loafer’s formality.

The loafer often features a saddle, or decoration, that consists of a plain strap, a strap with a slit, a  metal bit, or tassels. Its minimalist version, the Venetian, simply has the vamp exposed across the front of the shoe with no decoration. A signature characteristic of loafers is an elevated seam that follows along the shoe’s toe. A more casual variant of the loafer is the driving moccasin that usually has a softer, less structured look and features a dotted rubber sole.

The Dress Boot

The Ultimate Guide to Dress Shoes: Dress Boot

Built like your standard Oxford, the dress boot is generally the same shape with a longer shaft. This short, lace-up boot often features wingtip broguing on the toe and along its seams and rises over the ankle. This style traces its roots to the Victorian era when the choices in men’s shoes were very limited. During this time, men could only wear boots with day wear or pumps for evening wear. Because of the limitation of styles available to men, the Dress Boot became an intermediately formal dress shoe option that was worn to formal day occasions like tea or a formal lunch. Now, the dress boot’s place in menswear has remained quite similar as a great alternative to your typical dress shoe that’s perfect for formal day wear. For more casual occasions, lighter brown leather is acceptable, while for more formal occasions, stick to dark colored leather.

The Chelsea Boot

The Ultimate Guide to Dress Shoes: Chelsea Boot

The Chelsea boot originated from Victorian England and were made by shoemaker  J. Sparkes-Hall for Queen Victoria. The boots’ elastic siding allowed for them to be put on and taken off with ease, while still maintaining the refined silhouette of a laced boot. The Chelsea boot became the practical alternative to rigid Victorian boots of the time and soon became a  riding staple of the equestrian set. They found a modern revival during the 1960’s Mod trend where they adorned the ankles of pop-culture’s finest including, most notably, The Beatles.

These boots are ankle length with rounded toes and low heels. The vamp and the quarters meet near the ankle and are joined by elastic. The Chelsea boot has an incredibly clean look with the vamp and quarters each being made from a single piece of leather, keeping the stitching to a minimum. They have minimal to no decorative additions, maintaining the boot’s sleek and minimalist look. The simplistic look of the Chelsea boot can easily add a classic touch to jeans, but can also give a slightly alternative look to a tailored suit. A pair in polished leather can be paired either formally or casually, while you may want to reserve your suede pair for casual to semi-formal outings only.

The Chukka Boot

The Ultimate Guide to Dress Shoes: Chukka Boot

The Chukka Boot finds its origins within the game of polo, gaining its name from the seven and a half Polo playing period, called the “Chukker” or the “Chukka.” Chukkas resemble a shorter version of boots used during Polo, however it is thought that they were intended to be a more comfortable version that players could wear after the game.

Chukkas are ankle-length boots with two to three pairs of eyelets on each side for a lace-up closure. These eyelets allow for a snug fit around the ankle that, unlike regular boots, will not disrupt your pants’ shape. Chukka boots have a rounded toe, minimal stitching, and open lacing (similar to the derby). They are traditionally made of soft suede, however polished leather versions can offer a more formal look.

Chukkas, though similar, are not to be confused with desert boots. Desert boots are a much more casual version of a Chukka boot  with similar shape, but featuring a rubber sole instead of the traditional leather.

Though these are the least formal of the bunch, they can definitely hold their own in semi-formal or business casual situations. Once you try on a pair of chukka boots, you’ll find they are surprisingly comfortable alternative to the typical dress shoe.

The Opera Pump

The Ultimate Guide to Dress Shoes: Opera Pump

Popular during the Victorian era, opera pumps were used as formal evening wear. They are traditionally made of patent leather and are adorned with a grosgrain bow. Men would wear them with knee-high stockings and breeches to operas, dances, and other formal events. Though they are not as popular today, opera shoes will occasionally be seen at full-dress events on fashion conscious individuals.


Though you may be an aficionado on the types of shoes, it’s all about details when picking out the perfect footwear. It is in the details that you are able to show a bit of your personal style and allow for a bit of embellishment or none at all. When choosing your next pair of dress shoes, abide by the one golden rule: the toes of your shoes should be rounded and never squared.

cap toe, wingtip, plain toe, medallion, apron, split toe

Plain Toe

Plain toe shoes are as simple as it gets. The vamp is left unscathed, providing a very clean and minimalist look.

Cap Toe

A cap toe looks like a horizontally stitched line that divides the vamp of a shoe at the toe. In most cases this will actually be a separate piece stitched as the toe on the vamp, like a cap. The oxford is most noted for the cap toe, however it can be seen on various types of dress shoes.

Split/Apron Toe

The split toe, otherwise known as the apron toe, features a seam that begins in the middle of the shoe, around the toe, and ending at the middle of the shoe on the other side. This toe style is more common in casual shoes.


Medallion is a plain toe and with hints of brogue decoration at the toe.


This toe style has a winged cap that peaks in the middle of the toe. This toe style often features broguing in the center of the toe and along the seam of the cap.


Any shoe and toe style can have brogueing. Brogue simply refers to the decorative perforations in various patterns on dress shoes. Originally, the perforations were used to allow water out of shoes when crossing wet terrain, however they have now become solely a style statement. Brogueing is most often seen on oxford, derby, and monk strap shoes and is available in four different 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, take the shape of a wing-shaped cap, with the brogued cap coming to a peak opposite the toe, while its sides extend to the sides of the shoe. This styling offers a bold look that truly makes a statement.

Longwing Brogues

Longwing brogues are most commonly seen on the derby shoe. The shoe’s brogued cap takes on the same W shape with its with its sides extending down each side of the shoe all the way to its center seam in the back. This style takes the look of the full brogue and extends it down the length of the shoe.


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 offers a flourish of embellishment that is a little 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.


Obtaining a signature pair of dress shoes is an absolute essential of every man’s wardrobe. Pick a well crafted pair that expresses your personal style while remaining timeless. If you’re looking to add a little more dimension to your dress shoes, try out a new way of lacing them or a colorful pair of shoelaces to give them some unique flair. We’re certain that once you start your collection, one pair will hardly seem like enough.

Below is a full size infographic if you feel like sharing.

The Ultimate Guide to Dress Shoes