Aside from the menu above, you can also use the following quick reference before you continue scrolling:
- Formal Shoes
- Semi-Formal Shoes
- Casual Shoes
- Boots
- Shoe Formality By Color
Clicking on any of the above links will send you right to a subject area rather than a particular shoe. Note that we also cover shoe color as well as different shoe styles.
Furthermore, each shoe style has its own guide. If you want to learn more about a particular shoe, look for the link in its overview. Finally, boots have been separated from shoes as they’re their own entity even if their formality can be graded with shoes.
Most Formal Shoes
The following section includes a complete list of formal shoes in order from the most formal to the least formal:
Opera Pump
The opera pump is one of the last vestiges of court dress that is still in use today. Typically made in black patent leather but also available in smooth black calfskin, opera pumps are essentially slippers with bows at the top of the vamp. They’re worn with tuxedos.
They’re not for everybody, but for a more eccentric guy who attends black tie events, they’re just the right amount of formality and irreverence.
Oxford
The oxford (also known as a “balmoral” or “bal”) is one of the workhorses of the men’s shoe world. Its formality is derived from its closed-throat lacing system (fully explained in the previous link), which minimizes bulk and allows trousers to drape elegantly over a shoe. These shoes are typically worn with evening wear and suits.
Monkstrap
Monkstraps (and double monks) have been referred to as the “most advanced dress shoe” by many, and they’ve seen a huge resurgence in popularity in the past few years. More formal than a blucher but less formal than an oxford, they fasten with buckles as opposed to laces.
They’re also exceptionally versatile. Pair them with suits, denim, odd jackets and trousers, and even shorts if you’re wearing a sneaker version.
Derby
The derby shoe (also referred to as a “blucher“) utilizes laces just like an oxford. The difference, however, is that bluchers use an open-throat lacing system as opposed to the oxford’s closed throat system. It makes the shoe a bit bulkier, and thus more casual.
You can wear plain derbies with suits if you want to dress them down a touch, but they tend to do best with odd jackets and trousers or denim.
Brogue
“Brogue” is a corruption of the Gaelic wordbróg, which literally translates to “shoe.” It’s defined by its pinking and perforations, or small decorative holes punched into the lather. These holes used to be functional and allowed water to drain from the shoe after wading in marshes.
Broguing can happen on literally any style of shoe, not just lace-ups. It even occurs on boots and sneakers.
Though there are many different styles of brogue, the pinking and perforations themselves add bulk, heft, and an ornate design element, all of which serve to make the shoe more casual.
They can be worn with some suits but tend to look best with denim, casual trousers, and odd jackets. Particularly heavy brogues pair wonderfully with heavy tweed jackets.
Semi-formal Shoes
Venetian Loafer
Moving away from lace-up shoes, we get to slipons. The Venetian loafer is defined as any slipon that’s unadorned. They are free of broguing, straps, bits, or any other decoration. Just leather and seams.
As such, they are the most formal of all the slipon shoes when they have a dress sole and heel. In fact, in black patent leather, Venetians are one of the few sartorially correct options for black tie.
When they’re constructed without a dress sole and heel, their formality decreases.
Bit Loafer
Popularized by Gucci in the 1950’s, the bit loafer is one step down the formality ladder from Venetians. Characterized by a metal bit that lays horizontally across its vamp, bit loafers are great business casual shoes and also work very well for evenings out.
Penny Loafer
An Ivy League style classic, penny loafers belong in any man’s closet. Popularized by G.H. Bass as the “Weejun” loafer, they rose to notoriety in the 1950’s on Ivy League college campuses. They’re characterized by the decorative “saddle” that sits across their vamp, and there are many different styles of penny loafer to choose from.
Worn to the office or for a casual brunch, their name comes from the tradition of putting actual pennies in the strap.
Tassel Loafer
Simply slip-on shoes with decorative tassels hanging from the vamp, tassel loafers have long been associated with older men’s style. They are now being worn by younger men and look excellent paired with denim, casual trousers, and even shorts. In most business professional situations, however, they’re a bit too casual.
Casual Shoes
Driving Shoe
About as Italian as a casual shoe gets, driving shoes are moccasins with rubber nubs for a sole (these actual help you grip a car’s pedals better). While not ideal for walking from a longevity standpoint, they’re extremely comfortable and look great with casual trousers, denim, and shorts.
Boat Shoe
An American summertime classic, boat shoes (also referred to as “topsiders,” their name when sold by the brand Sperry) are casual shoes that still have a bit of structure to them. They’re made with a sole that will grip (but not scratch) a boat’s fiberglass, hence their name.
Available in a wide range of colors, boat shoes are a perfect shoe to wear with shorts and rolled up casual trousers.
Espadrille
Hailing from the Pyrenees region of Spain and France, espadrilles are essentially loafers with canvas uppers and a sole made from esparto rope. Originally a shoe for dock workers, it has become an ultra-casual summertime shoe.
Extremely popular thanks to the brand Tom’s, espadrilles can be worn with casual trousers, shorts, and even bathing trunks.
Sneaker
Sneakers need no real introduction as everyone and his uncle is familiar with them. Ranging from casual at the dressy end of the spectrum to athletic at the informal end, sneakers like Converse All-Stars or Adidas Stan Smiths should be relegated to denim, shorts, and casual chinos. Athletic sneakers should be worn for athletic endeavors and nothing else.
Flip-flops
Also known as “thongs” in places like Australia, flip-flops are super casual, onomatopoeic summer sandals that are most often paired with bathing trunks and shorts.
There is an ongoing debate regarding whether or not it’s appropriate to wear flip-flops in town with casual clothing. We invite you to take a look at our flip-flop guide for a more in-depth discussion.
Slides, a sandal that stays on the foot via an upper you “slide” into versus a thong that sits between the toes, is similarly casual and is subject to the same debate.
Boots
Chelsea
Named for the London neighborhood in which they were popularized, Chelsea boots are ankle-height boots that pull on and have no fastening mechanisms such as laces or buckles. Their clean, streamlined presentation is what makes them the most formal-looking of men’s boots.
Slim versions of this boots pair well with suits in cold weather, whereas chunkier versions are great with denim and thick sweaters.
Chukka
Another ankle-height boot, chukkas are fastened to the foot with laces, typically two or three eyelets’ worth. A step down the formality ladder from chelseas, dressy versions can still be worn with suits while casual versions can be worn with the most casual pair of jeans.
Riding
Relegated to the equestrian world, riding boots by brands such as Ariat are knee-high leather boots made specifically for horseback riding. They have no real application off of horseback but warrant a mention here.
Nevertheless, they’re reserved for formal equestrian occasions as opposed to the more relaxed Jodhpur boot. Whether it be hunts, dressage or other events, they’re typically worn with tight riding trousers and thick sport coats.
Outside of horse riding, their application is limited. However, they could be classified as a dressy-casual boot if paired well.
Jodhpur
The jodhpur boot has a strong equestrian history, as they were the boot invented to work with newly-invented jodhpur pants in the late nineteenth century. Characterized by a series of straps and buckles, jodhpur boots are relatively rare compared to chukkas and chelseas and are a bit more casual due to the bulk that their fastening mechanism has.
As for their equestrian role, they’re reserved for more daily and casual usage. Hacking, grooming and mucking out are all done while wearing Jodphur boots in order to preserve the owner’s precious riding boots.
Desert
Desert boots are casual chukka boots that have a crepe sole. Originating from Cairo bazaars, these were spotted by Nathan Clark while stationed in Burma, and he brought the design home to his family company. They were showcased by Clark’s at the 1949 Chicago Fair and were a hit.
To this day, they’re popular in a multitude of colors and materials and should only be worn with jeans and casual trousers.
Motorcycle
A mid-calf height boot with a harness and buckle closure, motorcycle boots are very casual due to their rough-and-tumble nature. Made to protect the legs and feet of motorcycle riders, they tend to be made of thick, strong leather and heavy hardware.
These are to be worn with jeans.
Duck
Invented by Leon Leonwood Bean, the duck boot is a waterproof boot with a rubber sole and a rubber/leather combination upper that was originally intended for use by hunters. Originally a lace-up boot, duck boots is available in pull-on and lace-up boots of varying heights and can be lined with shearling or Thinsulate for added warmth in the snow.
These are extremely casual and typically should only be paired with jeans. If you’re wearing them with your tailored clothes for a commute, that’s fine, but be sure you change into proper shoes once you get to your destination.
Shoe Color Formality, Ranked
If you’re curious about how to pair shoe colors with trousers, we have a huge comprehensive guide for every trouser and shoe color. We cordially invite you to take a look!
Black Shoes
Black is the most formal shoe color. The only classic option for tuxedos and very commonly seen on business suits, black shoes are ubiquitous.
While all shoes must be well cared for to maintain their good looks, black leather in particular starts to look tired quickly and thus requires extra attention when polishing and storing.
Dark Brown
Arguably just as dressy as black but offering superior style, dark brown shoes are one rung down the formality scale from black (it’s not appropriate to wear dark brown with a tux). Brown shoes are beloved for the patina they acquire over time, and they pair with everything black shoes pair with, except black.
Though they can be worn in any season, dark brown shoes work best in autumn and winter.
Cordovan
Both a material and a color, cordovan refers to a brown-ish burgundy shoe color. They pair with anything dark brown shoes pair with but are a touch less formal due to their lighter shade.
Navy Blue
Though rare, navy blue as a shoe color is relatively dressy due to its darkness. In a dress shoe situation, navy blue shoes pair well with navy and grey trousers.
Charcoal Grey
Another rare shoe color, dark grey shoes sit on the same rung of the formality ladder as navy and pair with the same color trousers.
Medium Brown
Medium brown shoes are extremely versatile and pair with just about any trouser you can think of. They’re relatively informal due to the lightness of color. While they can be worn to work in many offices, you should opt for a darker shoe if going to a job interview or funeral.
Tan
Even in the dressiest silhouettes, tan shoes have an air of casualness about them. These should only be worn in the spring and summer months.
Tan shoes pair beautifully with medium blue and light grey suits, making them great for warm weather weddings.
White
Technically only appropriate from Memorial Day to Labor Day, white shoes are very informal and should only be worn in the most casual of situations. It’s also helpful to keep your wear frequency to a minimum, as white shoes get dirty very easily and require particular steps to clean.
Non-standard colors (red, green, purple, etc.)
Other shoe colors like red, purple, green, or orange are the least formal available on the market. Essentially novelty colors, these are great for casual wear with denim and chinos. If you’re wearing a suit just for fun (not for business), a dress shoe in one of these colors can really take your ensemble into the stratosphere, stylistically speaking.
Conclusion
A shoe’s formality is dictated not by just one of the aspects mentioned above, but by considering them all simultaneously. The whole is truly greater than the sum of its parts.
We hope you found this guide helpful. If you have other questions about shoes, let us know, or check out some of our other footwear guides:
