The characteristic distinction of the best derby shoe is the construction of the upper part of the shoe where the laces attach. The lace eyelets are set into two side flaps that close over the tongue. This design was so common in the early twentieth century that it became the format most sneaker designs follow to this day.
The Derby Shoe is one of two general categories of leather dress shoes, the Oxford being the other. Derby shoes may have been replaced by sneakers for everyday wear a long time ago, but they are still a very useful tool in any man’s arsenal. They’re the fundamental shoe option to go with suiting or black tie. They also pair well with jeans and chinos for business casual or a night out. We’ve assembled a list of the best men’s derby shoes available for every occasion.
The American Classic
Alden Cordovan Plain Toe Blucher
Alden has been handcrafting leather footwear in Middleborough, Massachusetts since 1884. They are one of the most respected shoe companies in the world and their products are made to last a lifetime if properly cared for. At $820, the Cordovan Plain Toe Bluchers are an investment piece that will be the highlight of any outfit and can probably be passed down to you kids one day.
The English Originals
Crocket & Jones Highbury Plain Toe
Derby shoes were invented in England and Crocket & Jones still handcrafts their shoes the same way they did a hundred years ago. Buying an English-made derby is like buying a Swiss-made watch, the generations of craftsmanship is evident in every pair. Whether you wear them with a bespoke suit or a worn in pair of jeans, your feet will be the center of attention.
The Go-To Dress Shoe
Cole Haan Harrison Grand Cap Toe Derby
Cole Haan makes as reliable a dress shoe as your gonna find anywhere. Their Harrison Cap Toe Derby is a perfect go-to all-purpose dress shoe whether you need them for work, for date night, or for the rare formal occasion. If you only need one pair of dress shoes in your closet, this is a great option.
The All-Day Minimalist
Ecco City Tray Plain Toe Derby
Ecco designs their shoes with comfort as the primary goal. They make classic designs that can be worn all day, five days a week, without destroying your feet. Their City Tray Plain Toe Derby is ideal for a shoe, especially if you’re on your feet all day. They’re also great if you hardly ever wear dress shoes but comfort is your primary concern when you do.
The Almost Sneaker but Not
Børn Todd plain Toe Derby
For a while now, shoe companies have been making dress shoes with sneaker soles to make them more comfortable and functional. This evolution is not a bad thing but many of them veer too far into sneaker territory and lose the derby look. Børn nailed the combination perfectly with their Todd Plain Toe Derby. It’s a leather derby upper with a rubber sneaker sole that doesn’t detract from the classic aesthetic.
The Crepe Sole Comfort
Astorflex Coastalflex Derby
Crepe soles became popular with desert boots and wallabees. The crepe material provides a bouncy comfort to every step. Now you can get practically any style of shoe with a crepe sole. The Astorflex Coastalfelx is an excellent crepe sole derby in tan suede that looks great with jeans, chinos, or shorts.
The Perfect Denim Pairing
Allen Edmonds Nomad Buck Suede Derby
There is a timeless beauty to the pairing of tan suede and worn denim. The complementary textures and contrasting colors are a sartorial match made in heaven. Allen Edmonds Nomad Bucks will give your favorite pair of jeans a new life. Of course, they also look great with a suit, tailored trousers, or dark chinos.
Derby shoes were your grandfather’s sneakers and when you’re styling them it helps to think of them that way. They can be an every day shoe if you want to upgrade your look a bit. You know they work with suiting but they don’t have to collect dust in your closet between formal occasions. Swap a pair out where you would normally wear sneakers and you’ll see the improvement. Any of the options on this list are a good place to start based on your personal style and needs.
Also, you should always have a well kept pair ready for those formal occasions, but if you’ve got an alternate pair don’t be afraid to beat them up. A good derby can age like a good boot and look better with wear. Once you’ve spent some time in a derby, you might just wonder how you’ve lived most of your life in sneakers.
