The Ultimate Men’s Dress Shoe Guide The anatomy and style of classic men's dress shoes.
Having a great pair of dress shoes in your closet is not a luxury, it’s a necessity. Even men who default to casual shoes and sneakers will eventually need to suit-up. Opportunity favors the prepared.
This guide is intended to help you make a wiser choice on your next shoe purchase. Once you understand the differences between the options available, you will be half-way to looking your best at any event, interview, meeting, or date that requires a formal shoe.
Deconstructing the Dress Shoe
In order to understand a particular style, you should first understand the components that make up a dress shoe. Working from front to back, a dress shoe is divided into four parts: toe, vamp, facing, and quarter. It is the placement and construction of these pieces that help give a dress shoe its individuality.
Type of Dress Shoes
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 a 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 Gaining its name from its history at Oxford University, oxfords were a newer version of the popular Oxonians that were popular at the university circa 1800. This half-boot style was — at century’s turn – judged outdated, and students began looking for an alternative style. The oxford shoe was the fulfillment of longings for something modern.
The shoe is characterized by its facing being stitched under the vamp. This is called “closed lacing.” The facing’s placement provides a slim silhouette that hugs the foot’s contour. It is on account of its minimalism (and ability to go with just about everything) that the Oxford enjoys its popularity. For general everyday wear, there are many colors from which to choose, 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 them with a tuxedo or other formal wear, black patent leather is your best bet.
The One Piece Oxford is a variation on the classic oxford, constructed of a single piece of leather rather than various pieces sewn together. This style has only one seam connecting the piece of leather to the back of the shoe while maintaining the original oxford shape and signature “closed lacing.” The limited stitching gives a sleek and sophisticated look that adds to the shoe’s simple, no-nonsense style.
The Derby shoe, also known as the Gibson or the blucher, was originally intended as a sporting and hunting boot circa the 1850’s. At the turn of the 20th century, Derbies became accepted as appropriate footwear for the 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 placing of the face. The Derby shoe has the facing stitched on top of the vamp; with an oxford, tabs are sewn under the vamp. This construction, called “open lacing,” allows for a wider fit than is typical with an oxford. For many, this makes the Derby a more comfortable shoe. This simple detail has kept the derby reminiscent of its sporting roots, for which reason it is received as a less formal version of the Oxford.
The Monk Strap
A shoe with a monk strap is similar in shape and construction to an Oxford but in place of an eyelet closure, the monk strap has a wide swath of leather fastened across the front of the shoe. This is the “strap,” which is fastened with either a single or double-buckle closure. The shoe takes its name from the monks who originally donned them. The simple closed-toe design provided greater protection than the sandals traditionally worn by men in the orders.
How “formal” is a monk strap? All else being equal, the style itself lies somewhere between the Oxford and the derby. This classic alternative to laced dress shoes adds a certain panache to any outfit. While this has not always been the case, the monk strap is now regarded as a very versatile style of shoe style. It can be worn with cuffed jeans, or with the most dapper of suits. Monk strap attracts 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 decorative broguing.
The loafer is a moccasin-inspired shoe that is most recognizable for being a slip-on style. The loafer was originally intended as a casual house slipper made for King George VI of England. The loafer was neither acknowledged nor popular as a casual shoe until the King’s slippers crossed the pond. Manufacture of the loafer in the United States was underway in earnest by 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. This variant 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.
The loafer often features 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 version (the Venetian) has an exposed vamp absent embellishment or ornamentation. A signature characteristic of loafers (especially those nearer to a moccasin than a regal slipper) is an elevated seam that runs along the shoe’s toe. A very 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 to optimize wearer-comfort while driving.
The Dress Boot
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 often features wingtip broguing on the toe and along its seams, typically rising over the ankle. This style traces its roots to the Victorian era when men’s footwear options were limited. The dress boot quickly became an accepted dress shoe option, appropriate for formal daywear. The place of the dress boot in menswear has remained much the same, and it is an attractive alternative to typical dress shoe styles.
When is a boot dressy enough? It should be sleek, not too chunky, have laces thinner than those found on casual-wear boots, and should have soles which 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, their color doesn’t much matter so long as it compliments the suit. Unless you are an expert, assume that a suede dress boot is a contradiction (though it need not be).
The Chelsea Boot
The Chelsea boot originated in Victorian England, reputedly with shoemaker J. Sparkes-Hall (boot maker to the Queen Victoria). Then as now, the boots’ elastic gussets allowed for them to be pulled-on and slipped-off with ease, without compromising the refined silhouette of a laced boot. Indeed, the absence of laces contributed to their neat shape. The Chelsea boot became the practical alternative to the rigid Victorian boots of the age and quickly recommended themselves to the equestrian set. There was an uptick in sales the 1960’s when Mods took them from the paddocks to the pavements. Victorian naturalist Charles Darwin might have had a fondness for beetles, but The Beatles had a fondness for Chelsea boots. Thanks in part to blokes like them, the style remains popular today.
These boots are ankle length with rounded toes and low heels. The vamp and the quarters meet near the ankle and are joined by an elastic gusset. The Chelsea boot owes its clean, tidy look to the fact that – in dressier versions – the vamp and quarters are made from a single piece of leather. This keeps the stitching to a minimum. Classic Chelsea boots are absent decorative flourishes or embellishments. Their simplicity puts them in a class all their own: jeans get an upward lift, and traditional-style 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 Chukka has origins in the game of polo: it is the unit of time by which polo matches are measured. (A typical chukka is seven minutes long, and a polo match consists of four, six, or eight chukkas.) Some have said that chukkas resemble shorter versions of the boots worn by polo players, but it is claimed also that they were intended to be a more comfortable version of polo boots that players could wear after the game — think the original Uggs and surfers.
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 which, unlike regular boots, will not disrupt the shape of one’s trouser-bottoms. Chukka boots generally have a rounded toe, minimal stitching, and open lacing (similar to the derby). They are traditionally made of soft suede, but nowadays there are many versions from which to choose.
Chukkas are not to be confused with desert boots. Desert boots are a much more casual version of a Chukka boot and have a nearly identical shape. They are distinguished by soles that are not made of leather.
These are the least formal of the shoes we are discussing. They would not be appropriate for anything except casual attire, although pairs in high-quality leather compliment a smart-casual ensemble. Both chukkas and desert boots are exceptional.
The Opera Pump
Popular during the Victorian era, opera pumps were part of a formal evening wear ensemble. They are traditionally made of patent leather and are adorned with a grosgrain bow. Back in the day 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, worn by fashion-conscious individuals.
Dress Shoe Toe Styles
When making an investment in quality footwear, consider and take note of the details, because it’s all about details. As with everything relating to style, particularity about (and attention to) details enable you to bring elements of personality to your ensemble. 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 or pointy. There’s a time and place for this style of toe but we are now discussing investment in a pair of dress shoes.
Plain toe shoes are as simple as it gets. The vamp is unadorned. The resulting look is clean and unassuming.
A cap toe has a horizontally stitched line across the vamp of a shoe — it “caps” the toe. In most cases, this will actually be a separate piece stitched as the toe on the vamp, but sometimes the cap is accomplished by stitching. Many cap-toe shoes will be in the Oxford style, but the cap can appear on other styles too.
The split toe, otherwise known as the apron toe, features a seam that begins in the middle of the shoe, runs around the toe, and ends at the middle of the shoe on the other side. This toe style is more common in casual shoes.
The medallion style has a plain toe and 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 dress shoe style can have brogueing. Brogue simply refers to the decorative perforations in various patterns on dress shoes. Originally, the perforations were holes which were intended to allow water out of shoes: when yomping across crossing wet terrain (wet shoes being inevitable), the holes let water be squeezed out with each step. 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 Brogues / Wingtips
Also known as wingtips, the wing-shaped cap extends around to the outside of the toes.
Longwing brogues are most commonly seen 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.
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.
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.
Take Your Pick
A signature pair of well-made dress shoes is an essential possession. Choose a well-crafted pair, and choose wisely. Ideally, your selection will express your personal style, and “fit” with the ensembles you are most likely to be wearing. You can add a little more dimension to your dress shoes through creative lacing or the addition of a colorful laces. Not every man will be able to spend a fortune on dress shoes. As you consider your budget, we recommend taking into consideration how often you will be wearing them, and where you will be most likely to be wearing them. If use is likely to be limited mainly to the occasional wedding, funeral, etc., there’s no need to break the bank. If you are most likely to be wearing your dress shoes as part of your business/professional ensemble, spend a bit more than you’d like to. If you will be wearing them regularly, we recommend spending as much as you can comfortably afford to spend, and that you consider a well-made pair of dress shoes a small investment.
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