Know Your Dress Shoes

Categories Fashion

What’s the diff between an Oxford and a Derby? The dress shoe definitions you need to know.


Based on the Oxonian, a late 18th century boot style that became popular at Oxford University, Oxfords have evolved into the world’s most common dress shoe style and are available in a variety of materials, from canvas and suede to patent and calf leather. The primary characteristic is “closed lacing”, meaning the shoelace eyelet tabs are sewn beneath the vamp. (The vamp is the part of the shoe that starts behind the toe and encompasses the tongue and eyelets). The Oxford is more formal than the Derby.


2. Brogues

The word has its origins in the Old Irish “bróg”, which simply means “shoe”. But while they’re quite dressy today, brogues were originally pretty basic leather shoes designed with holes that would allow water to drain after Irish folk had gone a-walking across a muddy bog. Today, brogue means a low-heeled shoe characterised by decorative perforations and serrated details along the visible edges of its multiple pieces. Early in the 20th century, they were considered casual. These days they’re acceptable in most business or formal settings.


3. Monk Shoe

This dress shoe has no laces and is instead fastened with a “monk strap” featuring one or two buckles. Available in calf leather and suede, it’s slightly less formal than the Oxford but still very dressy. In fact, in 2014, The Wall Street Journal included monk shoes on its list of five essential menswear items, proclaiming them “the most advanced dress shoe”.


4. Derby

Also known as Gibson Shoes, these were originally hunting boots in the mid-1800s, though they became acceptable for city wear in the early 20th century. They contrast with Oxfords because they are constructed with a method known as “open lacing”, which means the shoelace eyelets are sewn on top of the vamp.


5. Chelsea boot

Chelsea boots date back to the mid-19th century and are the most enduring boot style worn today. They’re ankle-high, fit snugly and have elastic gussets for flexibility. Often found with a rear fabric tab or loop to help you pull them on.


6. Loafer

Also called “slip-ons”, these are the most casual of dress shoes. Loafers are constructed as low, laceless shoes, usually made of leather and sometimes decorated with tassels, or, in the case of Gucci, with metal. More explicitly dress loafers are designed to mimic the look Oxfords, though with elastic gussets and without laces.



7. Desert Boots

These are ankle-high boots that feature two or three eyelets with open lacing and are usually made with suede or calfskin uppers and sturdy rubber or leather soles. The get their name because they were worn by the British army in the African desert during WWII. Also known as “Chukka Boots”.


8. Boat Shoes

Invented in 1935, boats shoes—also known as deck shoes—are flat profiled footwear with non-marking rubber soles designed to grip on a wet deck. They’re usually made from canvas or leather treated with oil to be water resistant and boast sturdy stitching designed to last in the elements. The big rule? Don’t wear them with socks.


And The Three Main Toe Types…

A “plain toe” is the most simple and elegant, meaning no toe cap or brogue detail. A “cap toe” is a decorative piece of leather or stitched seam over the toe and is usually meant for business shoes. A “wingtip” is a pointed toecap that extends along each side of the shoe: while less dressy, it can be worn for formal or business occasions but to be honest, is unfashionable right now.