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Even if dress codes have changed dramatically, dress shoe styles for men actually haven’t changed all that much in the last hundred years. But, every now and then, we need a refresher. In this article, we’ll cover five types of dress shoes to have in 2022- even if you’re not wearing them every day. We’ll show you what colors to wear, what colors to avoid, and a few other ways to style them.
| Table of Contents |
| Five Types of Dress Shoes You Need: |
| 1. Oxford |
| 2. Derby |
| 3. Loafer |
| 4. Monk Straps |
| 5. Dress Boots |
| Bonus: Specialty Types of Dress Shoes |
What are oxford dress shoes? An “Oxford” is any type of shoe with a closed lacing system. This means the eyelets are punched into the quarter of the shoe, and the lace is then threaded through. This results in a streamlined, elegant profile around the foot. This usually makes it the ‘dressiest’ type of dress shoes.
Oxfords generally fall into four categories: the cap toe, the plain toe, the wingtip, and the wholecut.
The cap toe is distinguished by the piece of leather (the ‘cap’) around the toe of the shoe. How much of the vamp this cap covers varies depending on the brand and the lasting of the shoe. An American-style Oxford (say, the Allen Edmonds Park Avenue) has a shorter cap than a more aggressively-styled Oxford from a European brand like Magnanni. The cap toe is perhaps the easiest to style, and should be the first Oxford in your collection.
While not exclusive to Oxfords, the wingtip can be identified by the intricately designed cap featuring a point reaching backward toward the heel- creating a “winged” effect. These kind of shoes typically (but not always) feature broguing and pinking, which are the perforations and ridge-shaped designs on the cap. This ornamentation does make the shoe more casual, and usually suited toward outfits with chinos, slacks, and odd jackets. Jeans are also more than acceptable here, too.
| Further Reading on Jeans: |
| How to Wear Jeans and Dress Shoes |
The plain toe, as you might surmise, is characterized by the absence of the straight cap across the toe. It doesn’t necessarily make the shoe less streamlined, but does give a different look.
The wholecut is an unusual character in the dress shoe world. The upper is made from a single piece of leather, and the eyelets are punched directly into the shoe. Because it is made from such a large piece of leather, it’s difficult for a maker to conceal imperfections or blemishes- so the hide has to be good. Because there’s so little material, this is the most formal of the Oxfords. And, because it is so formal, it is the least versatile of this kind of shoe. You can wear them with odd jackets and trousers, but definitely skip the denim.
A black Oxford is arguably the first dress shoe a man should own. It should be a cap toe, without any broguing or other kinds of ornamentation. Even in this day of more relaxed dress codes, it’s among the easiest to pair with navy and grey suits. It’s the ideal choice for formal business meetings and funerals. We’d also suggest these would be just fine for a black-tie look as well.
When searching for a black shoe, in particular, do be mindful of the finish on the shoe. Overly shiny or patent leather-finished shoes are not suitable for business wear or separates. Please reserve those for black tie.
A pair of brown Oxfords is definitely worth having in your closet. We’d suggest a pair in dark to medium brown, with a quarter or half brogue. This allows you maximum versatility for more casual suits, chinos, odd trousers or jackets, and even to combine with some dark denim.
The oxblood or burgundy Oxford can be a kind of ‘wild card’ in your shoe arsenal. The colorway looks nice with any style of shoe mentioned above, as well as many shades for suiting. Oxblood Oxfords and a medium grey flannel suit can look particularly sophisticated- especially so if the suit happens to be double-breasted. These are a nice colorway for wholecuts, too.
A ‘derby’ style dress shoe is any shoe with an open lacing system. This means the eyelets are punched into two additional quarters stitched onto the vamp. Even when the laces are tied together, some of the tongue is visible. This gap between the quarters gives it the ‘open’ name.
These additional pieces of leather make the derby a little less streamlined and inherently more casual than the Oxford, but no less refined or versatile in a man’s wardrobe. Many men with wider feet or those that tend to swell throughout the day tend to prefer derby-style shoes to Oxfords, as it is easier to loosen them without disrupting the silhouette.
There exists a slight variation on the derby called the blucher. While they are commonly referred to interchangeably, they are *technically* not the same. A blucher is characterized by two pieces of leather stitched onto the vamp-without the separate tongue the way a derby does.
Derby shoes come in many of the same styles as oxfords. Many in mass-production will have some form of broguing or wingtip to them; however, higher end ready-to-wear or (especially) bespoke shoemakers will have a refined toe cap or even no cap at all on the toe.
Another common style of derby is the spectator shoe, shown above courtesy of Alden. This is identified by a two-tone finish-often in white or cream and brown. You can find them in suede or smooth leather.
Now that we’ve covered the characteristics of a derby and the subtle differences between it and a blucher, what are some colorways to consider?
While the classic “brown derby” actually refers to a restaurant chain and a style of hat, the dress shoe style is quite versatile and should be the first derby you purchase.
Look for something in a chocolate or coffee brown- few shades lighter than the brown pair of Oxfords. This is the ideal choice to pair with tweed suits, wool jackets and trousers, and chinos. They could also work nicely with solaro cotton or linen suiting as well. A wingtip or shoe with some form of broguing would be preferable here, too.
Tan derby shoes are a little lower down the formality scale, but can still be quite stylish. While we’d avoid wearing them with most forms of denim, they can also look nice with odd jackets in brown or olive, and especially with seersucker or other cotton suiting.
While ‘black’ and ‘casual’ are somewhat a clash in formality, a black plain-toe derby in polished calfskin is perfectly acceptable to wear with most black tie ensembles. It can look quite refined with black tuxedo trousers and a velvet dinner jacket in bottle green, burgundy, or gold.
A loafer is, essentially, any shoe without laces-a ‘slip-on’ type of dress shoe. It usually has a softer construction on the upper; however, the structured sole and low stacked heel help to distinguish it from a moccasin-style shoe.
Men's loafers tend to come in three general styles, with a few speciality varieties mixed in.
The ‘penny’ loafer fits the classic profile of soft upper and stacked heel. It may have a shorter, rounded toe box- or a longer, almond-shaped toe. But, a distinguishing characteristic of all penny loafers is the slotted apron across the vamp where a lace would usually go. One story of the ‘penny’ got it is how Ivy League students in the 1950s, who wore the shoes with button-down shirts and Harrington jackets, put pennies in the slots as a sign of rebellion against the conservative dress of their parents. Another competing (and contradictory) story suggests the fad started much earlier, when travelers started keeping pennies in the slot to use for emergency pay phone calls.
A second style is the tassel loafer- a loafer with a decorative tassel attached to the vamp where laces would usually go. The origin of this style is rather unclear- though modern interpretations seem to pop up shortly after the second World War as well. While, of course, the tassel can be attached and detach, it’s not meant to serve as a way to tighten or loosen the shoe. The size and shape of the tassel, as well as the size and shape of the toe, can vary: you could have a round-toe shoe with a small tassel, or an almond-toe loafer with a larger tassel.
A third common style is the horsebit loafer. Also known as the “Gucci” loafer, you can pick it out by the metal ‘horsebit’ across the vamp where a lace would usually be. Shapes are similar to those of the penny and tassel loafers. While the classic Gucci loafer has a rounded toe and a box that sits squarely in the middle between longer or shorter, a horsebit loafer with a slightly elongated toe box can look quite elegant.
Now that we’ve covered the basics, let’s address an elephant in the room: the square-toed loafer.
These kind of shoes rose to prominence in the mid-to-late 2000s. Designed for men who wanted to put as little effort into their formal/suited dress as possible, they had elastic on the upper to make it very convenient to get on and off. Considering the materials of many of these shoes, they didn’t stay on for long. The telltale characteristic of this footwear, however, was the severe square edge of the toe box. We urge you, dear reader, to remove these from your wardrobe if you still happen to have some in your collection. For further reading, GQ wrote an article titled The Square-Toe Shoe Must Die.
With that PSA out of the way, let’s talk colorways. If you’ve got black Oxfords and brown derbys taken care of, a pair of oxblood loafers is an excellent place to go next. Whether you choose penny or tassel is largely up to you. We’d argue a true penny loafer is a little more modern, but it does come down to personal preference. The same goes for the toe shape. If you are more traditional, select a shorter, more rounded toe. It looks excellent with a classic navy blazer and grey flannel trousers for a reason! If you lean contemporary, try a pair with an almond toe.
Deep brown loafers are also a great choice, and equally easy to pair with chinos or jeans on the weekend. Try them instead of sneakers for a lunch date.
Much like the derby, a black loafer can appear, on the surface, to be a contradiction in formality. But, a black Gucci loafer looks refined, elegant, and pairs beautifully with anything from suits to jeans.
| Further Reading on Loafers: |
| The Ultimate Guide to Buying & Styling Men's Loafers |
| How to Stylishly Wear Socks with Loafers |
A ‘monk strap’ is a shoe secured to the foot with buckles instead of laces via a strip of leather over the vamp. This makes it a rather interesting hybrid between a loafer (no laces) and a derby (open system). While the exact history and country of origin is ambiguous, the name does kind of give away who likely first wore this style of shoe: medieval monks seeking durable footwear.
In modern times, this style of dress shoe has fallen in and out of favor. It had quite the moment with the low-gorge lapels and wide shoulders of the 1980s, and became gradually less mainstream in the 1990s and early 2000s. But, by the early 2010s, the shoe became less a novelty and more a staple in the modern man’s wardrobe.
As the style is characterized by a buckle, the number of buckles and straps can vary. Most common are single or double monks, though the former is a little more formal than the later. Triple monk straps are sometimes seen, though they are likely on shoes with aggressive lasts and bold colorways.
Double Monk straps will usually (but not always) have a cap toe on them, although it is less common in single monk straps.
Noticing a trend here? Brown shoes are infinitely more versatile than black. With the bases in Oxford, derby, and loafer covered, you can feel free to branch out. If you tend to favor darker color combinators (navy blue and grey), go for a dark brown pair.
Conversely, if you prefer a lighter color palette, select something medium to lighter brown. A light brown, similar to the pair shown above with khaki dress socks, is a tremendously versatile type of dress shoe. Now is also the time to experiment with suede. A pair of dark brown double monk straps, in either suede or smooth leather, can be an excellent companion for anything from a three-piece suit to dark denim.
Oxblood can look particularly nice in a pair of single monk straps and grey flannel trousers. But, much like any loafer or oxford, err on the darker side here. An oxblood shoe can drift into “red” territory quickly!
| Further Reading on Color Coordination: |
| How to Match Your Socks, Dress Shoes and Pants |
| What Color Socks Go with Black Dress Shoes? |
| What Color Socks Go with Navy Blue Suits? |
Black buckled shoes have the unfortunate association with Pilgrims, and it may be hard to avoid comparisons here. However, medium to light grey sharkskin or hopsack suiting is an excellent blank slate to work with a pair of black single or double monk straps.
The words “dress” and “boot” don’t usually go together, but have taken on quite a following over the course of the last decade. A dress boot, generally defined, is one with a medium to low heel and the same general profile as an ordinary dress shoe-but with an upper shaft in the 4-6” height range.
A dress boot can come in both Oxford and Derby styles. An Oxford-style dress boots may also be called a balmoral, after the Royal retreat in Scotland. In the same manner as many boots, each of these will typically feature “speed hooks” for the top three or four eyelets. However, the laces are the same width as dress shoes to keep the profile streamlined.
Another variety is the Chelsea boot. Originally designed as an easy boot for Queen Victoria to slip on and off, this is a laceless boot with rubber elastic on either side of the heel shaft. It is, traditionally, a boot with an elegantly sloped upper and fairly low heel. However, some modern interpretations featured stacked heels and soles with heavy treading. The traditional interpretation is far more versatile, though.
Some manufacturers will also construct a monk strap-style boot with buckles. These are definitely rare, but can be a tasteful and interesting style if you choose one of the versatile colorways we mentioned above.
Speaking of colorways, dark brown is once again your most versatile option. It’s an excellent way to dress up your jeans or even to dress down a pair of suit trousers.
A pair of black boots, especially Chelsea boots, is a way to get creative with your suiting. Look for a more formal, smooth leather version with a low heel and almond-shaped toe box. A pair of black balmoral boots with a suede/nubuck shaft is also quite traditional for English formal daywear.
You may have just caught how this subtitle changed. Cordovan is a material as well as a colorway. True cordovan comes from a membrane in a horse’s hindquarters. While it can come in any color, really, the most traditional is a deep, dark reddish-brown. It takes a polish better than any other material- and tends to ‘wrinkle’ at pressure points instead of creasing. A pair of Cordovan boots, while a true luxury at well north of $500, will last more than a lifetime.
We’ve covered the basics of today’s most common types of dress shoes, the order to purchase them in, and the colors in which to do so. Once you’ve got those bases covered, though, the world of men’s dress shoes runs much deeper. Let’s cover a couple of specialty shoes to give you an idea.
While, technically, a slipper isn’t a dress shoe, there are a few varieties falling into that general category.
The most well-known-or perhaps infamous-of these is the Belgian slipper, sometimes also referred to as a Beglian loafer. Introduced in the United States by Henri Bendel (who also brought Chanel stateside) in the late 1950’s, they became a staple of country club prepsters throughout the 1960’s. They retained somewhat of a cult following among the upper crust, and the pairs you just had to have came out of Belgian Shoes NYC, a shop on 55th street in New York City. The shoe got a bad rap in the late 2000s as it was a favorite of fraudster Bernie Madoff, whose collection of some 300 pairs was auctioned off in the wake of his arrest and conviction. But, once you try a pair, it’s hard to go back.
A Belgian-style shoe is a very low shoe with a soft, unstructured upper. More casual versions have a rubber sole without a heel, and more formal varieties will have a leather one with a stacked heel. Many Belgian slippers will also have a little bow on the vamp, but a second unique characteristic is the oblong-shaped tongue. These shoes will work wonderfully with anything from a pair of light-wash jeans to a tuxedo.
Now to wrap up with the most formal of shoes- the opera pump. These high-gloss shoes are a perfect choice if you seek to take your tuxedo game to the next level.
Modeled loosely after European “court shoes” of the 17th and 18th centuries, these will usually have a satin or grosgain bow across the vamp- but may also have a penny loafer-style strap across the vamp as well. The last is usually long and elegant, but the cutout can be quite deep. The idea, of course, is that shoes are meant to be worn exclusively for indoor and formal leisure activities.
With all this talk about different dress shoe types, the perfect complement is an excellent pair of dress socks. Here at Boardroom Socks, we make some of the finest socks in the world. Each pair is woven right here in the United States with quality yarn in merino wool or long-staple cotton. We offer a wide variety of styles in over-the-calf or mid-calf to support any event that would require a dress shoe.
Thanks for reading.
Yours in Style,
Tony Gorga
If the airline lost your luggage and all of your socks, where would you start? We rebuild a sock drawer from the ground up.
