59 Awesome Derby Shoes for Men

Considering your shoes can make or break your look, it is essential to pick the right pair. Having a pair (or two or three) of sleek and timeless derby shoes in your closet can certainly make the decision easier. This style of shoe is ideal for work, your weekend, and every occasion, event, and style choice in between. 

Like Oxfords, derbys are a standard yet classic and comfortable dress shoe that is suitable for formal occasions as well as the right casual and smart casual looks. A pair of derbys can look just as good with jeans as they do with a suit. 

1. Black

Besides low-rise white sneakers, black derbys are one of the most versatile shoes that can take you from work to drinks to dinner to after dinner drinks. Black derbys come in a variety of designs and styles including matte leather, patent leather (Ooh! Shiny!), and suede, to name a few.

Wear your patent leather pair with gray trousers and your favorite band t-shirt in black or gray. Try a smart casual look with matte leather derbys, black ankle pants, and a short sleeve printed button-up shirt.

2. Boots

Did you know you can also enjoy your derbys in the form of a boot? They appear just like the standard design that you know and love, but with a taller shaft and an open lacing system, giving any outfit a sleek military touch. Keep it casual with distressed jeans and a t-shirt, perhaps throwing on a blazer if you feel that’s the right move. Or, wear dark indigo straight leg jeans with a button-up and two-toned brown and tweed derby boots for a more classic and vintage look.

3. Brogue

A brogue is a shoe that features decorative perforations and is available in many different styles of footwear, including derbys. A derby brogue has a bold, yet fashionable appearance and can be dressed up and dressed down. Remember, derby shoes are very versatile. Dress up your daily khakis and polo with chestnut brown derby brogues. Your fellow office husbands and wives will thank you.

4. Burgundy

Wearing your derbys in an atypical colorway, such as burgundy, with a standard outfit of jeans and a navy polo or button-up will turn your style game up a notch. Or, wear your burgundy derbys with tailored burgundy suit pants, a white and maroon striped button-up, with a navy blazer and pocket square that brings the whole color palette together. 

5. Cap Toe

This style of derby shoe features an extra piece of leather added to the toe. They can feature broguing around the cap-toe and sometimes a medallion. They tend to be considered more casual than formal, but style rules are meant to be broken. Wearing them with cropped wide-leg pleated pants and a linen short-sleeve shirt keeps you trendy and stylish.

6. Classic

Classic derbys are easy to wear. Opt for sleek, simple styles with minimal stitch detailing. Plain, leather, simple, done.

7. Dark Brown

Dark brown leather derby shoes are ideal for work and formal events. A brogue-style derby with decorative perforations adds a sense of formality as well. Wear your bespoke chestnut patina leather derby shoes with black trouser socks, light gray suit pants, and a black fitted button-up sans tie. Let your shoes speak for themselves.

8. Lace

Selvedge denim, a bomber jacket, and black matte derby shoes laced up make for a nice smart casual look on your next day off. Perhaps you have a formal event on the horizon? Patent lace-up derbys are the perfect way to finish off your tux look. Maybe your next event is slightly less formal? Pair your lace-up derby shoes with skinny tailored ankle pants and a white formal tuxedo shirt, no jacket, no tie, no pocket square, no cuff links; no problem.

9. Round Toe

The rounded toe is the most traditional and basic shoe shape. They tend to be quite spacious and comfortable, especially if your feet are on the broad or wide side. Since this toe shape is so simple, it can be innocuous, making this style of shoe easy to pull off for pretty much everyone.

10. Style

Using fashion to show off your style is part of the fun of getting dressed. Sure, keeping it simple for certain occasions can be the right move, but being able to wear your newest safari jacket and how it looks great with skinny black jeans, a black Oxford shirt, and your matte black brogue lace-up derby shoes shows off your unique style.

Are you jealous of that guy that somehow manages to pair his derby shoes with shorts and a blazer? Don’t be. Just be that guy. An indigo blue short and blazer set with a chambray blue t-shirt and slip-on brown derby shoes is the perfect way to ease into the look.

11. Suede

Yes, leather derby shoes are timeless and classic, but a suede pair can offer a more relaxed and contemporary feel, making them the perfect shoe for your favorite casual and smart-casual outfits. They are available in a variety of colorways, including brown, black, navy, white, burgundy, and tan to name a few. There is an option for every man and every event.

12. Suit

Derby shoes are the perfect go-to dress shoe for any suit because they can seamlessly work with a wide array of suits from casual to more formal. Dark brown and black leather derby shoes with minimal brogue detailing look best with more formal suiting while casual suits look better with a heavier brogue pattern and suede fabrications.

13. Vintage

You can either go with an entire vintage look or just vintage derby shoes. The choice is yours (feels good to be in charge, eh?). The more worn-in the leather is, the more vintage your derbys will look. 

Conclusion

Derby shoes can be dressed up or dressed down, but however, you choose to style them, make sure they fit properly. Wearing an ill-fitting shoe can take away from the stylish look you are trying to put forward.

They should fit securely across the arch with no slippage in the heel when walking. The fit across the ball of your foot will soften and stretch over time, so upon purchase, ensure the fit across that area is firm. Also, you do not want your toes to touch the end of the toe-end of your shoe. A thumb-width is ideal but can vary with each style.