5 Best Derby Shoes For Men That Are Classy And Stylish

It’s a pair that needs to be in every shoe closet. Perfect for business and casual attire, derby shoes are sought out by almost everyone.

It’s easy to see why. Made unique by its open lacing system and exposed ankle, derby shoes are a wardrobe staple. Soon enough, you’ll wear them to weddings, business meetings, and parties.

However, looking for the best derby shoes for men can be puzzling at first if you’re on a budget or unenlightened when it comes to fashion. That’s why we’re here to help.

Our Five Top Picks

An essential classic item, having a pair around is mandatory. Here are some shoes that are worth a look.

1.   JOUSEN Classic Derby Shoes

Made of faux leather, these glossy black derby shoes are a perfect addition to any formal clothing enthusiast’s closet.

A blistering heel is an issue many face when wearing the wrong shoe size for long periods. With an accurate fit, this pair of shoes ensures a comfortable lack of grinding.

On top of that, these shoes sport a stacked heel at 1.1” that provides great support. This prevents any foot cramps you might have to suffer from throughout the day.


  • Breathable
  • Made of faux leather
  • Described as ergonomically designed


  • Shoes have a strong chemical scent when first bought

2.   VOSTEY Men’s Dress Shoes Classic Derby Wingtip Brogue

These shoes optimize practicality for the workplace. Breathable with a soft insole, you don’t have to worry about any foot aches when standing for too long in office in these shoes.

With an elaborate decorative design, the wingtip adds a stylish nod. It’s eye-catching not only for its comfort but also for its classic brogue sensibilities.


  • Comfortable and breathable
  • Has a nice brogue touch
  • Accurate fit


  • Has an offensive chemical odor when first bought

3.   Rockport Men’s Derby Room Wingtip Shoe in Brown

This is another stylish and polished pair with a full brogue wingtip. Readily available in a rich deep brown, they’re ideal for a sharp business casual look.

Flexibility is an advantage in these shoes. Get ready to pair them with casual slacks for a sleek everyday look. Going to work? Then put on a suit and step into meetings in these shoes.

Most importantly, they don’t sacrifice comfort for style. They’re roomy and well-cushioned. Foot aches on long days are no cause for worry with these shoes.


  • Near perfect fit
  • Comfortable
  • Lightweight


  • Easily worn-out soles

4.   Alexis Leroy Casual Lace Up Men’s Derby Shoes

If you’re intimidated by the stark formality of leather dress shoes, then this black lace-up pair is worth a look.

It lends itself easily into different types of outfits. You could transform it with a pair of straight cuffed jeans into stylish everyday streetwear.

On top of its ability to adapt itself according to each outfit, it ensures maximum comfort and size compatibility.


  • True to size
  • Comfortable
  • Casual


  • Easily creased

5.   Rockport Men’s Derby Room Perf Cap Toe

With a perf cap toe, a unique touch is added to this refined pair of camel-colored derby shoes.

Yet, looks aren’t all these shoes have to offer. Its lightweight soles are slip-resistant, providing a solid grip on all surfaces.

100% leather is what these Rockports are made of. They’re designed to be easy to maintain and care for, extending its life and wear significantly.


  • The holes aren’t permeable so it’s safe to wear in the rain
  • Comfy
  • Offers good support


  • Lacks removable insert

Where Did They Come From?

With its open lacing system and its sturdy nature, the derby shoe could only have sprung out of the needs of individuals who prioritized comfort and practicality. Theories, however, differ.

Muddy Origins

The origins of the derby shoe vary from source to source. With all the questionable theories regarding the beginnings of derby shoes, a popular one claims that they were developed by Gebhard Leberecht von Blücher, who was a Prussian army officer during the Napoleonic wars.

Another theory muddles matters even further. This one credits the derby shoe origins to the 14th Earl of Derby, who commissioned his shoemaker to design a pair of shoes that would fit his wide feet.

Accordingly, the result was a pair of open-laced derby shoes that guaranteed comfort and functional wear.

Becoming Regular Footwear

However, derby shoes were only truly popularized in late-1800s England. Originally intended to be worn during hunting and sporting, they quickly became a defining aspect of every gentleman’s repertoire.

By the early 1900s, they had transformed into popular everyday footwear due to their unrestrictive nature, which is credited to their open-lacing system.

How to Wear Derby Shoes?

These shoes aren’t confined to the workplace. Sleek and timeless, there are numerous ways derby shoes could be worn.


Opt for a simple pair of leather derby shoes when heading to formal occasions. Whether it’s an office party or a business meeting, you’ll look dapper in a slim pair of shoes with sharply-cut dress slacks and a blazer.

Dark colors, such as brown or black, are your obvious choices in such circumstances.

Smart Casual

Dressing down derby shoes is just as easy as dressing them up. Throw rigid formality over your shoulder by looking for colors such as beige or camel. If you’re feeling bold, grey or cream are uncommon choices that you should look at.

As for designs, shoes with brogue wingtips are recommended. A chunky pair will also maintain an easy-going look. In this case, chinos, sweaters, and coats are your obvious choices for clothes.


They’re elegant and effortless, adding a smart finish to a casual look when paired with the right outfit.

Whether you’re looking for a practical pair like VOSTEY Men’s Dress Shoes Classic Derby Wingtip Brogue, or a casual one like Alexis Leroy Casual Lace Up Men’s Derby Shoes, looking for the best derby shoes for men can often be a rewarding and easy task.

When it comes to options, the sky’s the limit. What only remains for you is simple. You only have to try some shoes out.