Best Men’s Dress Shoes: Top 10 Picks to Buy Online

What Defines Formal Dress Shoes?

Dress shoes aren’t simply defined by a single characteristic but a multitude of various considerations. Below, we’ll take a look at the contributing factors that render a shoe dressy or not.

You can use the guide below for dress shoes but for a general overview, you can refer to our full shoe formality guide.

Practicality

Firstly, the extent of which a shoe can be considered “dressy” is by how functional it would be in everyday life. In short, the least versatile shoes that fulfil no practical role are considered the most formal.

Meanwhile, shoes with an utility function such as most types of boots and shoes that can be worn outdoors are the most casual. For instance, sneakers are for athletes, boots are for workers and so on.

However, there are exceptions to this rule. Take the example of Brogue shoes that were originally designed with perforations that improved drainage when walking through marches. This style has been largely appropriated by the ruling class and today is relatively dressy.

Nevertheless, it has retained its outdoor connotations and is therefore one of the least formal dress shoes.

Conversely, delicate opera pumps and tuxedo slippers are wildly impractical for wearing outdoors. They are therefore restricted to the city and indoors and would be unimaginably useless in a more rustic environment.

As such, they are considered more formal because their use can only be reserved for special occasions that expect the wear of exceptional garments.

Leathers & Materials

Regardless of style, the leather and material used to make a shoe will play a very significant role in its formality. In many ways, this ties to the previous consideration as the most rugged and resilient materials are considered the least formal.

Meanwhile, delicate and pristine materials such as patent leather and velvet are the most formal. These are usually reserved for the most exceptional dress codes and will be rarely worn on a daily basis.

For example, it would look particularly odd to see a regular business suit paired with patent leather Oxford shoes. However, you can go with smooth calf skin shoes for them to be considered dressy depending on the circumstances.

As a general rule, the rougher the material, the less formal it becomes. Once you begin wearing anything that isn’t smooth leather such as pebbled leathers, canvas and suede, things can become very casual indeed.

The same can even be said for soles. As rubber soles are cheaper and more practical on a daily basis, they’re considered much less formal. When dressing up for formal occasions, it may be expected that the soles are leather instead.

In fact, the choice of leather can have a profound impact on the shoe’s formality and even override the style’s initial level of dress. For instance, suede Oxfords (if such a thing exists) become much less formal than calfskin Derby shoes.

Shoe Color

Finally, shoe colour is another factor that we delve into in great detail on our shoe formality guide.

In short, the darker the colour, the more formal it is. With black being at the top as the most formal colour choice, you can work your way down to dark brown and cordovan as mildly less formal options.

As you begin to find yourself in medium browns and tans, the colours are considerably less dressy and begin to become quite casual. Once into typically non-leather colours, such as white, red and greens, you’re immediately in a decidedly casual dress code.

Dress Shoe Scale Of Formality

As mentioned above, the formality of a shoe greatly depends on its materials and finer details. However, a general rule of thumb is to refer to the following scale:

1. Tuxedo Slipper & Opera Pumps
2. Oxford Shoes
3. Wholecut Shoes
4. Monk Strap Shoes
5. Chelseas & Other Boots
6. Brogues & Long Wings
7. Derby Shoes

Simply use the links above to jump to a particular shoe style and learn more about it.

Tuxedo Slippers & Opera Pumps

Although several different styles, the most formal shoes are the least practical as explored above. Made from either patent leather or velvet, tuxedo shoes are sleek and elegant with a delicate touch.

Some tuxedo shoes, known as Opera Pumps, even feature a decorative bow across the top. Meanwhile, tuxedo slippers are simply velvet slippers with a leather sole.

You can learn more about the different types of tuxedo shoes with our dedicated guide.

Oxford Shoes

A staple shoe style reminiscent of Wall Street and the City of London, Oxfords are a classic and one of the most formal styles out there. Although mostly defined by their closed-laced throats, they will often feature a cap toe.

The cap toe is an extra piece of leather that’s stitched over the toe area, which is often buffed into a fine sheen. Sometimes, they can even be given a mirror shine.

Also known as Balmoral shoes, they can be worn for just about anything including and above business professional. For instance, a patent leather Oxford is ideal for particularly formal events including White Tie.

Learn more about this shoe style with our guide to Oxford shoes.

Wholecut Shoes

Technically a type of Oxford shoe because of its closed-lace throat, a Wholecut is considered a debonair and elegant style. They’re often quite formal as they’re made from a single piece of leather, which must be of premium quality in order to work.

Overall, wholecut shoes are quite expensive as despite using less leather, the craftsmanship is very demanding. Therefore, they’re also quite rare to find.

Reminiscent of Italian styles, they’re a relaxed alternative to Oxfords and somewhat flashier. You can learn more about this particular style with our dedicated wholecut shoe guide.

Monk Strap Shoes

Featuring either one or two buckles, monk strap shoes are a firm favourite among the most style conscious men. Today, double monk straps are the most popular. However, both are influential shoe styles.

Monk strap shoes can greatly vary in appearance with different areas for placing the buckle as well as the materials used. More rustic styles will be inherently more casual. Meanwhile, you can find black monk straps with very fine straps that are more elegant and thus more formal.

You can learn everything about this shoe style through our detailed monk strap guide.

Chelseas & Other Boots

By definition, boots are a type of utilitarian footwear. Therefore, they’re considered generally less ornamental and more casual because of their practicality. However, as we’ve said, you can render a style of shoe dressier depending on its construction and choice of leather.

Typically the most formal boot style are Chelseas, which are a recent style popularised by The Beatles in the 1960s. However, we’ve instead featured lace-up dress boots above because their construction is reminiscent of Brogues with their detailed ornamentation.

Wingtips & Brogues

An old Scottish classic, Brogues are highly-decorative shoes that feature ornamentation known as pinking and perfing. When speaking generally, these terms fall under “broguing” as they’re so intertwined with the shoe style itself.

Originally, brogues were peasant shoes and the perforations were functional in that they helped water drain off the shoe rather than soak into the leather. Therefore, they’ll always be more casual than formal dress shoes.

Nevertheless, their level of formality can largely depend on the leather and lacing system. For instance, you can find open-throat Derby-style brogues in suede, which are decidedly laid-back. Another well-known style of brogue is the Longwing.

Meanwhile, wingtips are shoes which feature additional stitching across the toe that look like a bird’s wings. A largely American term sometimes used for brogues, wingtips are a more urbanised style that feature no perforations or pinking. They’re also associated with the early 20th Century.

A common style of wingtip is the Spectator, which is a two-tone shoe. This can be very formal when made from monochrome patent leather. However, it can also be very casual if made from pebbled or suede leather.

If you want to learn more about either shoe style, you can read either our guides on Wingtip shoes as well as Brogues.

Derby Shoes

Finally, the antithesis of the Oxford is the Derby or Blucher shoe. Unlike the Oxford, which features a closed-lace system, Derbies have open laces. This means that the eyelets are found on an extra piece of leather that is fixed on either side of the throat.

Because of this more primitive and rugged design, Derby shoes are inherently less formal and more casual. However, when worn properly, they can be relatively dressy and certainly usable in most business professional settings.

If you want to learn more, head to our Derby & Blucher shoe guide.

What Next?

Now that you have learned about the best dress shoes that you can buy, have you considered other situations where you may need to build out your wardrobe? Check out some of our guides below to learn more:

• Best Men’s Summer Shoes
• Best Summer Dress Shoes For Men
• Men’s Business Casual Shoes
• Best Boots For Men