Elsewhere on the site, formality is covered in detail including guides on tuxedos and dress codes. However, they focus little on shoes. This article will deal with different formality levels of shoes. Here, you will find various shoe styles ranked from formal to casual. Generally, a shoe’s true formality is a function of three things: style, material, and color. For instance, a black patent leather oxford is more formal than a brown calfskin oxford. Similarly, a black patent leather Plain Slippon is more formal than a black calfskin oxford. Although it may be tricky, our guide will help. Just remember the rule of thumb that throughout tailored clothing, formality is typically a function of simplicity and a lack of bulk.

The following list includes shoes and boots that are the most formal.

• Oxfords
• Monkstrap
• Chelsea Boot
• Derby
• Brogue

There are several options when it comes to semi-formal shoes. Below is a list of shoes styles that are considered semi-formal:

• Plain Slippon
• Penny Slippon
• Tassel Slippon
• Chelsea boot

Casual shoes and boots range from a driving shoes all the way down to flip flops. Here is a list in order of formality:

• Driving Shoe
• Moccasins

The oxford (also known as a “balmoral” or “bal”) is one of the workhorses of the men’s shoe world. Its formality is derived from its closed-throat lacing system (fully explained in the previous link), which minimizes bulk and allows trousers to drape elegantly over a shoe. These shoes are typically worn with evening wear and suits.

Monks have been referred to as the “most advanced dress shoe” by many, and they’ve seen a huge resurgence in popularity in the past few years. More formal than a blucher but less formal than an oxford, they fasten with buckles as opposed to laces.

They’re also exceptionally versatile. Pair them with suits, denim, odd jackets and trousers, and even shorts if you’re wearing a sneaker version.

The derby shoe (also referred to as a “blucher“) utilizes laces just like an oxford. The difference, however, is that bluchers use an open-throat lacing system as opposed to the oxford’s closed throat system. It makes the shoe a bit bulkier, and thus more casual.

You can wear plain derbies with suits if you want to dress them down a touch, but they tend to do best with odd jackets and trousers or denim.

“Brogue” is a corruption of the Gaelic word bróg, which literally translates to “shoe.” It’s defined by its pinking and perforations, or small decorative holes punched into the lather. These holes used to be functional and allowed water to drain from the shoe after wading in marshes.

Broguing can happen on literally any style of shoe, not just lace-ups. It even occurs on boots and sneakers.

Though there are many different styles of brogue, the pinking and perforations themselves add bulk, heft, and an ornate design element, all of which serve to make the shoe more casual.

They can be worn with some suits but tend to look best with denim, casual trousers, and odd jackets. Particularly heavy brogues pair wonderfully with heavy tweed jackets.

Moving away from lace-up shoes, we get to slipons. The Plain Slippon is defined as any slipon that’s unadorned. They are free of broguing, straps, bits, or any other decoration. Just leather and seams.

As such, they are the most formal of all the slipon shoes when they have a dress sole and heel. In fact, in black patent leather, Venetians are one of the few sartorially correct options for black tie.

When they’re constructed without a dress sole and heel, their formality decreases.

An Ivy League style classic, penny Slippons belong in any man’s closet. Popularized by G.H. Bass as the “Weejun” Slippon, they rose to notoriety in the 1950’s on Ivy League college campuses. They’re characterized by the decorative “saddle” that sits across their vamp, and there are many different styles of penny Slippon to choose from.

Worn to the office or for a casual brunch, their name comes from the tradition of putting actual pennies in the strap.

Named for the London neighborhood in which they were popularized, Chelsea boots are ankle-height boots that pull on and have no fastening mechanisms such as laces or buckles. Their clean, streamlined presentation is what makes them the most formal-looking of men’s boots.

Slim versions of this boots pair well with suits in cold weather, whereas chunkier versions are great with denim and thick sweaters.

About as Italian as a casual shoe gets, driving shoes are moccasins with rubber nubs for a sole (these actual help you grip a car’s pedals better). While not ideal for walking from a longevity standpoint, they’re extremely comfortable and look great with casual trousers, denim, and shorts.