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How To Wear Casual Derby Shoes? Styling Tips & Much More

Casual Derby Shoes

Casual Derby Shoes are a must-have for every men’s wardrobe. No matter if it’s a formal suit, casual jeans outfit, or a blazer look, the classic derby shoe style will complement all of them equally. Making them a perfect match for any occasion all year long.

Derby shoes have no match when it comes to versatility. However, this quality sometimes backfires and figuring out the appropriate derby shoe style for casual or formal occasions becomes quite a task.

Therefore, to help you out in your next styling venture, here is a list of all the ways you can wear casual derby shoes like a pro!

What Are Derby Shoes?

Before, we head to the actual topic knowing the basics are necessary. So, let us first know what is a derby shoe. Historians narrate this shoe style to be born in the early twelfth or sixteenth century.

The distinctive feature of casual derby shoes is their open-lacing system. The lacing style with eyelets stitched on the top is considered the only differing factor between the derby and oxford shoes. But, this is not entirely true. The derby shoes are more than that.

The design embraces two quarters sewn separately on the vamp with the eyelets. However, there is a neat gap between the vamp and quarter even when the shoes are all laced up. For this reason, these shoes are often called open-lacing styles.

The open lacing system is often referred to as a business casual shoe style but derbies are an exception. These versatile shoes can be paired as casual or formal shoes depending on the formality of the event.

Are Derby Shoes Formal?

Derby shoes have an open lacing system which is considered a more casual lacing style than closed-lacing oxford shoes. However, just like Oxford, derbies can also be worn formally with suits at a semi-formal wedding party or a business meeting. 

But, for a severely formal setup like an event with a black-tie dress code sticking to the usual patent black oxford is a wise choice. After all, you do not want to lose your gentlemen’s look by making the wrong choice of footwear.

Choosing An Appropriate Derby Shoe Style?

If you are a newbie and do not know anything about derbies. Here are all the important features you need to consider when getting your hand on the perfect pair to match your shoe needs.

1. Color 

Color is the most crucial factor for deciding whether or not a derby style is appropriate for you. The darker colors are considered to be more formal than the lighter tones. So, choose accordingly.

For formalwear, brown or black derby shoes are a safe choice. However, for casual occasions go with tan or grey derby shoes men.

2. Detailings

As a general rule of thumb, the simpler the shoe style, the more formal it looks. So, if you want to wear your black derbies at a formal setup avoid brogue or wingtip designs. Going for a simple plain-toe leather derby will work in this case.

However, for smart casual or casual outfits such as a blazer or sports coat look, brogue are a perfect casual derby shoe style. So, make the buy considering the formality of the occasion.

3. Material 

You can find derby shoes mainly in two materials, the one is suede and the other is leather. Suede is an appropriate choice to pair with casual or smart casual attires. While for formal wear leather shoes will work well. 

However, the type of leather is also an important element to determine the formality of your shoes. For Instance, patent leather shoes are considered more formal than calf leather material.

4. Size 

Before pinning down the perfect derby shoe style, ensure that it fits well into your foot by walking around in them, for a few minutes. While choosing the right leather derbies do not go for a size up, as the leather has a tendency to stretch with time. 

Types Of Derby Shoes

Although men’s casual derby shoes are a versatile shoe style, not all derby shoes are appropriate to be worn at formal events. There are many different types of shoes to match the formality of the occasion. So, let’s find out what derby shoe style fits your footwear needs perfectly.

1.  Brogue Derby 

A brogue shoe, is a simple derby shoe having brogue details in its design. Broguing is small perforation carved into leather for decoration and aesthetics. The broguing details come in a variety of designs from simple toe brogue to full brogue which exhibits all around the shoe broguing details.

If you are looking for smart casual footwear, brogue derbies are all you need. Whether you want a sophisticated look or are up for some sturdy style, brogueing helps you add texture and personality to your entire outfit.

2. Chunky Derby Shoes 

With the raging popularity of trainers and leather sneakers, people started exploring more and more options in smart casual shoes fashion, which led to the innovation of chunky derby shoes. 

These shoes depict a smart formal vibe with their distinctive dress shoe design, whilst looking casual because of the chunky sole.

3. Derby Boots 

For all those guys who want to exhibit a rugged and polished look with their winter attires without looking too formal, derby boots are all you need. They are work-friendly, you can wear them to your fieldwork and to the after-work night outs with friends without compromising on your style and comfort.

4. Plain-toe Derby 

The plain derby, as the name suggests, has a minimalist design with no heels, no toe-caps, and no extra embellishments. The plain-toe derby design is an actual derby style that can easily be distinguished on the basis of primary characteristics. 

Out of all the other colors and styles of men’s shoes, plain-toe brown or black derby shoes men are considered the best men’s derby shoes for formal occasions.

5. Cap-toe Derby

The cap-toe derby has a cap-toe design in the same or different shade. This derby shoe style is more appropriate for casual occasions because of the characteristic toe cap. So, never dare to mix them up with your formal attire.

Wingtip Derby 

A wingtip derby consists of a pointed-toe ‘W’ or ‘U’ shaped cap. Often or not these design details run all over along the sides toward the heel cap. This is why they are called wingtip boots. The design is very similar to the wingtip brogue with a slight difference in the vamp and eyelet positions on the vamp.

How To Wear Men’s Casual Derby Shoes?

Casual derby shoe styles can be worn with a variety of different dress codes without going against formal dress code rules. Here is how you can pair them up with your everyday casual clothes to suit your style and the need of the occasion.

Business Formal Attire 

Business Formal Attire 

If you want to make a lasting impression at a job interview or want to assert confidence at an important business meeting, wear smart business shoes with suits. Men’s black derby shoes are an appropriate choice in such situations, for a rugged and polished look. 

However, try to opt for charcoal, burgundy, or navy blue suits other than black or charcoal with your derbies, as they are more suitable for semi-formal occasions. Going for a pin-stripe or other suit patterns will also be a good idea to add definition to your entire look.

Semi-formal Dress Code

Semi-formal Dress Code

Derbies can be a great footwear choice for many semi-formal dress code events like a wedding reception or a cocktail party. Opting for brown or black derbies with your semi-formal suit is a foolproof formula to be a head-turner at your next event.

However, for black-tie formal events try to play by the rules and opt for derbies. Wearing a pair of patent leather oxford is a wise choice in this situation.

Smart Casual Outfits 

Smart Casual Outfits 

Mens casual derby shoes are stylish footwear to pair with your everyday smart casual outfits. You can wear them with your button-down dress shirt, blazer outfits, and chinos for a sophisticated yet casual vibe.

Wingtip, brogue, and cap toe are some of the few derby styles that are most suitable to be worn with your smart casual workplace outfits.

Derby Shoes And Shorts 

Derby Shoes And Shorts 

Derby shoes have a very casual vibe and can be paired with most everyday outfits but are not very good footwear to wear with shorts.

However, a few derby styles like canvas or suede leather derbies in tan or blue color can be worn with summer shorts outfits. If you want to make a fun style statement with your corduroy shorts outfit, wearing derbies can be a game changer.

Casual Derby Shoes With Jeans 

Casual Derby Shoes With Jeans 

If there is one outfit that can be styled effortlessly with casual derby shoes without any prior fashion knowledge, they are jeans. Whether it is a summer t-shirt look or a preppy dress shirt with a tie, derby shoes with jeans are an outfit combo that will never disappoint you.

FAQs – Casual Derby Shoes 

Can Derby Shoes Be Worn Casually?

Yes, you can wear derby shoes casually with all your everyday outfits. Whether it is a casual day at work or a day out with friends, wear your derbies with your jeans, chinos, khakis, and slacks for an extremely casual and aesthetic vibe.

How Should A Derby Shoe Fit?

Derby shoes should feel snug and comfortable on your feet. There should ideally be a one-finger gap between your toe and the shoe frame. The best way to check the fit is to place your finger between your heel and the shoe sole.

Are Derby Shoes Comfortable?

Derbies are considered the most comfortable among all the other dress shoe styles. The larger toe area provides a comfy and snug feel for all the big-foot gentlemen, making them the most appropriate footwear to wear with your everyday casual clothes.

How Do You Know If Shoes Are Too Big?

The easiest way to find out whether or not the shoes are too big is to see how much space you have left inside your shoe after wearing them properly. If the space is much more or less than one finger than your biggest toe finger then the shoe size is not right for you.


Casual derby shoes are a must-have footwear style for everyone. While there are countless derby shoe styles available, choosing the right one that meets your needs, sometimes becomes difficult.

While men’s black derby shoes are considered appropriate for business professional and semi-formal occasions, you can wear brogue or chunky derby shoes with your casual and smart casual outfits for an effortlessly chic look. 

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