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How To Wear Derby Shoes With Chinos [7 Tips]

Both of these items are titans of menswear. Owning a pair of each would be a smart move by any measure. You’re about to learn how to wear Derby shoes with chinos in the most effective way possible. 

Let’s get to it. 

Derby Shoes And Chinos: An Introduction

Before we go further, it’s important to know exactly what Derby shoes and chinos actually are in the first place, as they’re often poorly understood/mislabelled. 

Derby shoes are dress shoes with large leather strips or “quarters” sewn onto the sides. They contain the shoelace eyelets and are sewn on top of the vamp, creating a flap-like open lacing system. 

brown derby shoes
Image From Deposit Photos

It’s this open lacing system that defines the Derby shoe. While it was traditionally considered casual footwear thanks to the comfort of its lacing system, it’s now frequently worn with business suits as well. 

Chinos are pants made from the twill fabric “chino cloth”. They were originally made from 100% cotton, but cotton-synthetic blends are extremely common these days. 

chinos and sweater
Image From Shutterstock

Derby shoes and chinos have one key feature in common – versatility. 

They both tread the line between casual and formal so well, making them appropriate for a variety of occasions, events, and settings. 

How To Wear Derby Shoes With Chinos (7 Tips)

These tips should serve you well when combining the two. While it isn’t complicated, having a foundation of knowledge is the key to pulling it off in the most effective way possible. 

1. Get The Dress Code Right

Before you land on the Derby shoes and chinos combo as your outfit of choice, it’s important to make sure it’s appropriate in the first place. 

Consider the setting you’re dressing for. 

There are certain dress codes where Derby shoes and chinos just wouldn’t be appropriate. They may not be outright forbidden, but they definitely wouldn’t be a good choice. 

Here are the dress codes where you should avoid Derby shoes with chinos: 

  • Formal – While Derby shoes may be a reasonable choice, chinos should never be worn to formal dress codes where a suit would be necessary. 
  • Very Casual – It may not look terrible, but Derby shoes and chinos would often look awkward and too formal when worn with a vest or hooded sweatshirt. 

Here are the dress codes where Derby shoes with chinos would often be ideal: 

  • Smart Casual – Think dates, garden parties, nights out, and mid-level restaurants. Polo shirts, Henleys, and Oxford shirts are commonly worn. 
  • Business Casual – Both Derby shoes and chinos are ideal items to wear in casual office environments where suits are too much and jeans aren’t enough. 

In a way, this should come as no surprise. 

Both Derby shoes and chinos fall somewhere in between casual and formal. It makes sense that the dress codes they’re ideal for are the “middle ground” dress codes – smart casual and business casual. 

Once you’ve determined that Derby shoes and chinos would be appropriate for the setting you’re dressing for, the next step is to get the combo right. 

2. Choose The Right Chinos

While chinos will all have the same feel and general aesthetic, some pairs do look “smarter” or more formal than others. 

It may not be that obvious, but it’s noticeable. 

When you’re choosing a pair of chinos to wear with your Derby shoes, it’s important to consider how casual or formal the setting you’re attending is. 

We’ve talked about how Derby shoes with chinos are a good option for smart casual and business casual dress codes. 

But the same pair of chinos you could wear to a smart-casual setting like a restaurant may look too casual to wear to a business-casual setting like a modern office or workplace. 

Here are some features to help you differentiate more “formal” looking chinos from more “casual” ones: 

  • Center creases down the pant legs look more formal than flat-front chinos
  • Cuffed hems will always look more casual
  • Slimmer and more tapered fits look more formal, while baggy chinos look casual
  • Decorative stitching and visible seam details look more casual
  • Patch pockets look more casual than welted or jetted pockets
  • Darker, neutral colors look more formal. Bright and bold colors look more casual

Here’s an example of a more “formal” pair of chinos on Amazon as an example: 

Now, here’s an example of a more casual pair of chinos on Amazon. Notice the baggier fit and flat-front legs. The suede Derbys also look more casual than the leather ones above. 

The bottom line here is this – not all chinos are created equal. A single pair of chinos may be perfectly fine for one setting but not for another. 

The same goes for Derby shoes – I’ll be talking about that in more detail later on. 

3. Careful With Color

When wearing Derby shoes and chinos, it’s important to consider the color of both. 

Chinos traditionally come in a light brown color (i.e khaki), but you can find them in practically any color you can think of. 

This is arguably the most versatile color, as you could easily wear them to both smart casual and business casual settings. In fact, khakis are a classic item of business casual attire. 

But otherwise, the darker the color, the more formal they’ll look. Charcoal grey and navy blue are good options for the chinos when you want to make them look smarter. 

The same goes for Derby shoes. The darker they are, the more formal they’ll look. When you’re dressing for business casual, dark brown is a fantastic and versatile option, while lighter shades of brown would also be fine. 

semi brogue derby shoes
A tan brown pair of semi-brogue Derbys. Notice how they look more casual than the plain, dark brown pair earlier on.

Image From Deposit Photos

Black Derby shoes would usually look too formal and are a better option when wearing a formal suit – not chinos. 

When you’re dressing for a smart casual dress code, you’ve got more options when it comes to color. 

Feel free to go for lighter, brighter, and bolder colors for both your chinos and your Derby shoes. 

However, just remember that sticking to neutral colors will make it so much easier to coordinate the two with other items you may be wearing.

Examples of neutral colors include white, olive green, khaki, grey, sage, and navy blue. 

4. Leather Or Suede

When selecting the perfect pair of Derby shoes to wear with chinos, it’s important to consider the material. 

Your main options range between “shinier” grains of leather like calfskin or cowhide, and more napped ones like suede. 

Shinier Derby shoes will look smarter and more formal than more rugged Derby shoes with less sheen. 

Because of this, when wearing Derby shoes and chinos to a business casual setting where you want to dress up (a little), go for calfskin or cowhide. Suede will often look too casual. 

However, suede Derby shoes can look great with chinos when you don’t need to dress up that much. 

suede brogue derby shoes
Suede brogue Derby shoes

Image From Deposit Photos

They’re an excellent option for smart-casual settings. 

The napped texture of suede pairs very well with the rugged texture of chino cloth. They sync pretty flawlessly, as long as the combination is appropriate for the setting you’re dressing for. 

5. Brogue Works Great

Brogue Derby shoes are a great option when wearing chinos, but it’s important to go overboard with them when it may not be appropriate. 

Once again, considering the event or setting you’re dressing for is the crucial factor here. 

“Brogue” is a term used to refer to the decorative perforations (i.e tiny little holes) you often find on dress shoes like Oxfords and Derby shoes. 

Full brogues (i.e wingtips) have a W-shaped toe cap with perforations lining the “W”, as well as the edges of the quarters along the sides. They’ll also have a “medallion” – a fancy, spiraling pattern of perforations on the toe cap itself. 

wingtip derby shoes
Wingtip Derby shoes

Image From Deposit Photos

Semi-brogues have fewer perforations and have a horizontal/straight toe cap, not a W-shaped one. The perforations will line the toe cap and there will also usually be a medallion. 

Quarter-brogues have a straight toe cap with perforations lining the edge of the toe cap but have no medallion. 

As you’d imagine, the more brogue-ing you’ve got, the more “formal” the Derby shoes will look. 

When wearing Derby shoes and chinos, choosing a pair of brogue Derbys is often a great option. 

It’s just important to know how far you can go with it. 

In general, it’s best not to go further than semi-brogue Derby shoes when dressing for a business-casual dress code. Wingtips (i.e full brogues) will often look too casual. 

When you’re dressing for a smart casual dress code where you can experiment a little more, feel free to go for wingtips. In fact, they’re an excellent way to stand out and work incredibly well with chinos. 

6. Switch Up The Laces

This may sound like it’ll take up way too much time, but it actually becomes pretty quick once you get the hang of it. 

Don’t get me wrong – this isn’t something you need to do when wearing Derby shoes and chinos. It’s just a great way to change things up and show that you go the extra mile when it comes to style. 

Changing the laces of your Derby shoes should be done in a tasteful way, but should also aim to produce contrast between the laces and the body of the shoe itself. 

You want the laces to stand out. 

It’s important to note that should really only be done for smart-casual dress codes, not business-casual. 

A pair of dark brown Derby shoes with red laces may look a little strange when you’re attending an office meeting or a conference. 

But when you’re wearing Derby shoes with chinos to a smart-casual setting like a party, restaurant, or date, changing the laces is a good option when you want to make the outfit stand out. 

A useful tip would be to try to match the laces to a different item of clothing you’re wearing at the same time, such as the chinos, polo shirt, or blazer, for example. 

7. Polos, OCBDs, And Sports Coats

When wearing Derby shoes and chinos, there are certain upper garments that just work so well. 

It’s important to get this part right, as choosing the wrong items to go up top could potentially ruin all the hard work you did with your Derbys and chinos. 

When considering what else you should wear, once again, the dress code is the most important factor. 

Here are a few examples, split by dress code: 

  • Smart Casual – Polo shirts, Henley shirts, sports coats, denim jackets. 
  • Business Casual – Oxford shirts (OCBD), cardigans, blazers. 

There are plenty more, but those are some of the more common items people wear. 

It’s interesting to see how varied these items are. This goes to show just how versatile the Derby shoes and chinos combination really is. 

Conclusion 

Hopefully, that’s everything you could possibly want to know about wearing this classic combination. 

It’s hard to go wrong with. But using these tips to your advantage should ensure that you pull it off in the best way possible. 

Enjoy.