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.
DECONSTRUCTING THE DRESS SHOE
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.
TYPES OF DRESS SHOES
The Oxford Shoe
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 Gaining its name from its history at Oxford University, oxfords were a newer version of the popular Oxonians that were popular at the university in 1800. This half-boot style became outdated and students looked for an alternative style that was more current, thus the oxford shoe was born.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 characterised 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 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 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 is a moccasin-inspired shoe that is most recognisable 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 popularised 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
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 coloured leather.
The 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 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
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.