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What You Can (And Can’t) Wear With Derby Shoes

Derby shoes can make or break an outfit. But their versatility can’t be denied. You’re about to learn exactly what you can wear with Derby shoes and how to pull them off in the most effective ways possible. 

It’s hard to make a faux pax with a pair of Derbys. But it’s important to get the right pair and to combine it with an outfit that makes sense after taking the setting and formality into account. 

No two pairs of Derbys are the same. 

That’s why it’s important to understand what makes a pair “formal” and what makes a pair “casual” before you start experimenting with outfits. 

So, I’m going to go through that first. Then, use specific examples to demonstrate what you can wear with Derbys, as well as what you can’t. 

Let’s get to it. 

Are Derby Shoes Formal Or Casual?

Derby shoes are generally considered to be more formal than casual. Features that make a pair of Derby shoes look more formal include leather uppers, the absence of brogue detailing, and a black or dark brown finish. 

On the shoe formality scale, they’re seen as less formal than Oxfords but more formal than loafers and monk straps. 

Having said this, it’s important not to generalize when it comes to Derbys. 

While Oxfords are categorically considered to be the standard of formality, Derbys are a lot more versatile. 

It may be true that they lie toward the formal end of the spectrum, but it’s definitely possible to combine Derby shoes with smart casual outfits. 

All that’s important is that you understand the 3 principles behind what makes a pair of Derby shoes look more “formal” and what makes it look more “casual”. 

These are the color, the detailing, and the material. Let’s discuss them one by one. 

1. The Color

This is by far the most important factor when it comes to determining whether a pair of derby shoes looks more formal or casual. 

Put simply, black and dark brown shoes will always look more formal than lighter colored shoes. 

Here’s a formal-looking pair of black leather Derby shoes on Amazon

Black is the most formal and the least versatile. It’s hard to pair black derby shoes with anything other than a suit. 

Lighter colors give you more options. For example, you could quite comfortably wear a pair of tan brown Derby shoes with cuffed chinos and a rolled-up OCBD shirt to a summer soiree. 

Here’s a more casual-looking example on Amazon to illustrate the point:

It’s possible to get Derbys with even brighter and bolder colors – the more “out there” the color, the more casual it’ll look. 

2. The Detailing 

Cutting right to the chase, brogue patterns and other detailing on the derby shoe will make it look more casual. 

The more plain and simple the derby shoe looks, the more formal it’ll seem. 

Take this into account when choosing a pair of Derbys. 

If you’re looking for a pair to wear with a business suit or tux, it’s generally best to avoid brogue patterns. 

But if you’re looking for a pair to wear with a smart casual sports coat combination or something even more casual, brogue patterns are exactly what you should be looking for. 

In those instances, the more casual they look, the better. 

3. The Material 

Put simply, leather will always look more formal than suede. Given that these are the two main materials you’ll find derby shoes in, it’s important to realize this right from the outset. 

Yes, it’s possible to find Derby shoes in even more casual materials such as canvas fabric, but it’s a little more unusual. 

If you’re looking for a more “formal” pair of Derby shoes – definitely go for leather over suede. 

However, if you’re looking to pair the shoes with more casual or smart casual outfits, suede is a great way to go. 

Remember, there are different types of leather as well. Black patent leather is the shiniest and most formal looking. Calfskin, on the other hand, has a rougher texture to it and less sheen. 

So, to sum that all up: 

  • Formal Example  – black or dark brown leather with no pattern
  • Casual Example – lighter and brighter colors, suede, and brogue, or other detailing/embellishment. 

Now, let’s talk about some specific outfit examples. 

Can You Wear Derby Shoes With Shorts? 

It’s generally best to avoid wearing Derby shoes with shorts. This is because shorts simply look too casual to combine with even the more casual pairs of Derbys. It’ll usually lead to an awkward match. 

Although Derby shoes do come in different colors, materials, and patterns, they will ultimately always be considered a “dress shoe”. 

Dress shoes lean toward the formal end of the spectrum. 

Shorts, in no way, shape, or form, can be considered to be anywhere near the formal end of the spectrum. They are gloriously casual and can’t be expected to be anything more. 

Even the more casual pairs of Derbys with suede uppers, brogue patterns, and light/bright colors will be tough to combine with shorts. 

Having said that, if you were intent on trying out this ambitious combination, it’s important to seek out those casual features in your derby shoes. 

It’ll be easier to get away with a suede (or ideally canvas) pair of Derby shoes than a leather pair. 

In addition, look for more “formal” looking pairs of shorts. Chino shorts may be an option. 

But at the end of the day, more casual summer shoes would be more appropriate – think boat shoes, moccasins, espadrilles, or suede penny loafers. 

Can You Wear Derby Shoes With Chinos? 

Derby shoes can be worn with chinos and the two often work very well together. A wide range of Derby shoes ranging from casual to formal would be appropriate to wear with chinos. 

I often say that chinos and Derbys are a match made in heaven.

It’s just so hard to go wrong. Chinos strike such a fine balance between formal and casual, just like Derby shoes do. 

The pair works especially well in smart casual settings and in sports coat or blazer combinations

The beauty of wearing Derby shoes with chinos is that there’s such a wide range of derby shoes you could potentially go for. 

You could go for brown leather with or without brogue patterns. Alternatively, you could go for lighter-colored, suede Derbys and the chinos would be “casual” enough to pull it off. 

Black leather Derbys would probably look too formal to wear with chinos, however. You’d find it hard to combine black leather with anything other than a suit. 

But other than that, you’ve got quite a lot of freedom. 

Can You Wear Derby Shoes With Jeans? 

Jeans can be worn with Derby shoes that have more casual features such as suede or canvas uppers, brogue detailing, and lighter, brighter colors. 

It would be harder to combine jeans with more formal-looking pairs of Derby shoes. 

There are no two ways about it – jeans are casual. They’ll always be casual and you can’t expect them to be anything else. 

There’s really no such thing as a “formal” looking pair of jeans. 

Because of this, it’s important not to wear them with Derby shoes that are on the more formal end of the spectrum. 

More specifically, avoid wearing jeans with leather derby shoes, especially black and dark brown ones. 

These derby shoes are simply too formal to wear with jeans. 

It’s possible to get away with lighter and brighter colored leather derby shoes. In fact, it can actually work pretty well. 

But more “casual” materials such as suede or even canvas would be a lot more appropriate and easier to combine with jeans. 

In addition, Derby shoes with interesting detailing and patterns (eg. brogue) would make them look even more casual and appropriate to wear with jeans. 

Here’s a casual-looking pair of brogue Derbys on Amazon to show you what I mean: 

Ultimately, it’s definitely possible to wear Derby shoes with jeans – but you do need to put some thought into the specific type you choose. 

The same goes for the type of jeans you choose. Jeans come in a wide variety, ranging from more casual pairs to less casual pairs. 

More casual-looking jeans have distressed or ripped finishes and lighter colors, while darker-colored jeans have a less casual look to them. 

Given that Derby shoes are more commonly considered “dress shoes”, pairing them with less casual-looking jeans would appear to be a better match. 

Can You Wear Derby Shoes With A Suit? 

Derby shoes can easily be worn with a wide variety of suits. Formal suits are more appropriately worn with black or dark brown leather derby shoes with minimal brogue detailing. The more casual suits are better worn with suede Derbys or those with heavy brogue patterns. 

Ultimately, derby shoes often make the perfect dress shoe. They seamlessly fit with a wide range of suits ranging from smart casual to formal. 

You need to take the type of suit you’re wearing into consideration when choosing the right type of derby shoe to combine it with. 

If you’re going for a more formal suit – you’ll want a more “formal” looking pair of Derby shoes. 

Alternatively, if you’re going for a more casual suit, you’ll want a more “casual” looking pair of Derbys. 

Here’s a quick rundown of formal vs casual suits. 

Formal suits are usually made from wool – it’s possible to tell from the shine you usually get from the finish. Worsted wool is a common form that’s used – it doesn’t wrinkle easily. 

Here are some other features you’d usually find in a formal suit: 

  • Darker and more solid colors
  • The jackets have more structure, with heavy lining and padded shoulders
  • The pockets are usually jetted or flapped and not patched
  • The lapels are usually peaked or shawl. 
  • You’ll often find sharp center creases down the pant legs

Here’s an example of a formal suit on Amazon. Note that the shoes in the image are actually monk straps and the image is simply to demonstrate what a formal suit looks like: 

Casual suits, on the other hand, often have very different features: 

  • The colors and patterns are lighter
  • The jacket often has a lighter lining and less structure
  • The shoulders look more natural and often have less padding
  • The fabric used looks less “shiny” and wrinkles more easily. For example, linen, cotton, or wools such as flannel or tweed. 
  • The jacket is more likely to have patch pockets
  • The suit pants won’t necessarily have center creases and the seam details of the inner leg may be more visible. 

Here’s an example of a casual linen suit on Amazon

Try to match the type of suit to the type of Derby shoes. 

For example, if you’re going for a more formal suit, consider a black or dark brown leather pair of Derby shoes with minimal brogueing or other patterns. 

If you’re going for a more casual suit, consider a more casual pair of Derbys. This may include a suede or canvas pair in a lighter or brighter color. It could also include a pair with plenty of brogueing. 

Can You Wear Derby Shoes With A Tux? 

Derby shoes can be worn with a tuxedo. Plain Derby shoes in black patent leather and with no broguing or embellishments would be the most appropriate style to wear with tuxedos. 

Although times are rapidly changing, it’s hard to deny that black patent leather Oxfords are the top choice for a tuxedo. 

But nowadays, it’s common to find other styles of shoes made of different materials being worn with tuxedos as well. 

Loafers are a popular choice. Velvet slippers are also more frequently worn than you might initially think. 

But Derby shoes are equally appropriate. 

“Plain” Derby shoes are considered the most formal, with no broguing, cap toes, or heel caps. 

They would be the best type of Derbys to wear with a tuxedo if you were simply looking for a safe bet. 

It’s also important to note that while black patent leather is considered the most obvious choice to wear with a tuxedo, they’re not very versatile. 

They’d really only be suitable to wear to black tie events. Let’s face it – many of us (myself included) don’t attend those all that often. 

It’s perfectly fine to get yourself a pair of black patent leather Derbys. But if you’re looking for a more versatile pair that you could also wear quite comfortably with business suits, well-polished black calfskin will probably also be fine. 

It may be less flashy, but you’ll put them to far better use over the long run. I know – it’s technically matte and not traditionally considered “shiny” enough for a tuxedo. 

But try them out and see for yourself. If it’s well-polished it’ll probably look absolutely fine and most people usually won’t notice the lack of shine in any case. 

It’s a personal decision – but black patent leather or well-polished calfskin would be your best options when it comes to wearing Derbys with a tux. 

By the way – people often look for “wholecut Derbys” to wear with tuxedos, as wholecuts often look exceptionally sleek and formal. 

It’s important to understand that Derbys by definition can’t be wholecut (i.e made from a single piece of leather) because they all have separate quarters attached to the vamp. 

Bluchers are the closest thing to “wholecut Derbys” – they’re technically usually made from a single piece of leather but do still have the open lacing system you’d find in Derbys. 

What Socks Should You Wear With Derby Shoes? 

The best socks to wear with Derby shoes are cotton full-length crew socks or over-the-calf socks. As Derbys are usually worn with trousers, it’s wise to avoid no-shows, ankle socks, and even short crew socks. 

Ultimately, it’s best to keep the sock length relatively long when it comes to wearing Derbys. 

You want to avoid skin peeking out under the hem of your pants when wearing Derby shoes. As they’re generally considered a “dress shoe”, this would look awkward. 

Follow this rule-of-thumb regardless of whether you’re wearing chinos, jeans, or slacks. 

Although you could probably get away with short crew socks, the safer bet would be to go for full-length crew socks or over-the-calf socks.

Crew socks go as high as the middle or upper calf. They’re the most versatile and can be worn with both casual and formal wear. 

Over-the-calf socks are seen as the most formal and would be the most appropriate type to wear if you were rocking Derbys with black tie. They end just below the knee and won’t pull down or bunch up over time. 

At the end of the day, the fabric you choose doesn’t matter when it comes to wearing socks with Derbys. The sock length matters a lot more. 

To play it safe, go for cotton or wool. Yes, silk, cashmere, bamboo rayon, and even micro modal are options. But keep things simple and inexpensive. 

Cotton is the most common and will be the most versatile as well. It’s stretchy, soft, strong, and retains heat. You can wear them with both casual and formal wear. 

Wool is also an option – it’s usually a little more expensive, but wrinkle-resistant and also absorbs moisture. 

Conclusion 

Derby shoes can ooze sophistication – but it’s important to combine them with the right ensemble. 

Hopefully, you now have a much better idea of how to do just that. 

Enjoy.