There’s a world of formal footwear available to you. Here, we’ll tell you about all of the different types of dress shoes.
We’re deep into the age of fashion casualization. It was moving slowly at first. But it seems as if we headed in that direction in lightspeed around the time technology started to move in lightspeed. It’s no coincidence that the tech industry is a famously casual one.
Many of us probably live lifestyles that don’t call for a formal shoe that often. Smart casual is even starting to overtake business casual as the go-to dress code for many offices.
But dress shoes will never be irrelevant. We may wear them less than we used to, but it’s good to know what your options are. One type of dress shoe may better express your personal style than another type!
So, here’s a reminder of the types of dress shoes available to you.
Different Types of Dress Shoes
Here are all of the common (and not-so-common) dress shoe types you can choose from!
The Oxford Shoe
The Oxford gained popularity in the 1800s. Students at elite schools, Oxford included, started wearing them as a more casual, comfortable option over the common dress boots of the time.
Today, they’re a classic and safe dress shoe that isn’t always trending but is certainly always relevant. This makes them perfect for people new to the dress shoe game, as well as the highly experienced.
They’re a traditional lace-up, defined by the closed lacing system. This means the eyelet tabs are sewn under the vamp.
These days, Oxfords come in a variety of materials, including leather or suede, and can be equipped with traditional leather outsoles as well as rubber soles.
The Derby Shoe
The derby shoe is similar to an Oxford, except that it has open lacing. This means the eyelets are sewn over the vamp, not under. This allows for a wider fit and a more relaxed, broad aesthetic.
They’re definitely more casual than Oxfords, but both can be worn with either a suit or jeans. I’d say the derby has a more workhorse quality about it, though, while the Oxford is more traditionally dressy.
The Loafer
No shoe represents smart casual and business casual better than the classic loafer. Still, it’s technically a formal shoe, albeit a less formal one than traditional lace-ups.
A loafer is just a laceless, slip-on dress shoe. It’s typically made from regular leather or suede, and there’s a wide range of loafers out there, some more formal than others.
There are two ways to decide whether a loafer is more dressy or more casual.
First, the sleeker and pointier a loafer is, the more formal it is. So, an Italian-style leather model compared to a square-toed suede? The latter is the more casual choice.
Second, more detail means less formal. Still, it’s all about balance. So even a bit loafer, with its ornamental hardware, can be more formal than a penny loafer.
Perhaps the bit loafer is a whole cut, made from a minimal single piece of leather, with a slim silhouette, while the penny loafer is a square toe with beef rolls.
Here are a few common loafer styles:
- The penny loafer is defined by the saddle on its vamp. It’s a classic American design that can be worn casually or formally, depending on how detailed it is (does it have beef rolls?) and its silhouette (how slim or wide is it?). We also have an excellent round-up of some of our favorite penny loafers here.
- The horse-bit loafer features metal ornamentation that looks like a horse-bit snaffle. This shoe was popularized by Gucci and had a resort-chic vibe about it.
- The tassel loafer is any style that’s adorned with a tassel or two on the upper. How formal or how casual it is depends on what else is on the upper.
- The kiltie loafer has a decorative fringe on the vamp, making it one of the more casual options. It’s one of the few dress shoes that look natural with shorts, in my opinion.
- The Venetian is a whole cut, slipper dress shoe. It’s highly formal and minimal, and I personally think you can get away with wearing a black pair with a tuxedo.
The Monk Strap Shoe
A monk strap shoe is one that has straps that go across the upper instead of laces. They’re a bit like belts since they buckle in.
This style of dress shoe can come as a single monk strap, a double strap, or, more rarely, a triple strap. As always, the more details there are on the upper (or, in this case, the more buckles there are on the upper), the less formal it looks.
The monk strap shoe is pretty versatile since the hardware makes it wearable with workwear-adjacent casual clothes like jeans and moto jackets. However, a clean, slim model is still perfectly appropriate with a suit and tie.
Check out our round-up of the best monk strap shoes here!
The Brogue Shoe
The brogue shoe is really just a derby or an Oxford (or any dress shoe, really) that features prominent decorative perforations. These perforations are called broguing.
Farmers on the British Isles added perforations to their shoes so that water wouldn’t well up in their footwear. As such, brogues are definitely a more casual type of dress shoes. They’re definitely livelier than your average model, though.
There are four kinds of brogues.
- The semi brogue, or half brogue, has a perforated toe cap and perforations along most of the stitching. It also has decorative broguing at the toe area called a medallion.
- The quarter brogue doesn’t have a medallion and doesn’t even always have broguing at every single stitched area. It’s the most minimal and most formal.
- The wingtip, which is so distinct, some might give it its very own category, has a W-shaped piece of leather on its upper. The arms of the W dip down into the sole area. The reason why it can technically be categorized as its own style is that it doesn’t always have broguing (but most models do).
- The longwing is similar to the wingtip. It has that W-shaped piece of leather stitched to the upper. However, the arms of the W go all the way around the shoe, connecting in the back. Therefore, it has “longer wings.”
The Wholecut Shoe
The whole cut shoe is technically just an Oxford that’s built with one single piece of leather.
This makes it more minimal and more formal than a regular Oxford. As a bold choice, I like to wear my brown whole-cuts with my tuxedo.
By the way, I wear Ace Marks Whole-Cuts. Read my hands-on review here.
Dress Shoe Types: The Dress Boot
So basically, a dress boot is any of the above shoe styles, loafers aside, of course, except with a boot collar. This means it covers the ankle, serving as a more secure piece of footwear. It’s also more ideal than below-ankle shoe collars on colder days.
The Traditional Dress Boot
The most traditional dress boot is one that has a derby or Oxford upper style. When you wear them with suit trousers, it’s not always immediately obvious that you’re wearing boots until your hem goes up when you’re sitting or walking.
A lot of dress boots also feature wingtips and brogues for a look that really leans into the functional aesthetic.
The Chukka Boot
When it’s made out of leather and has a traditional leather outsole, the chukka boot can be worn as a dress shoe. Of course, the slimmer the silhouette and the pointier the toe, the better.
A suede chukka is a good option for a smart casual situation and you can even wear more formally-styled calfskin chukkas with a suit.
Chukkas are ankle-high boots with open lacing and a simple eyelet design featuring two or three pairs. They were possibly originally used for polo, which definitely gives them a sporty origin. Still, the association with equestrianism also gives them a stately air.
In our roundup of chukka boots, a wide range is represented, from formal to casual.
The Chelsea Boot
The Chelsea boot is a super minimal, close-fitting ankle boot. It’s laceless and features elastic side panels that stretch to let your foot in. It also often has a pull tab or pull loop on the back for convenience.
Like the chukka, not all Chelsea boots are dressy. However, the clean, minimal template lends itself to formalwear. If the boot is slim, constructed from leather, and comes with a heeled leather outsole, you can wear it as a dress shoe.
FAQs
Still, have questions about dress shoe styles? We’ve got you covered. Here are some oft-asked questions — and their answers, of course.
What Is Classified as a Dress Shoe?
A usually minimal leather shoe with at least a low heel and leather sole that isn’t a work boot, sneaker, or sandal.
What’s the Difference Between Oxfords and Brogues?
An Oxford is a closed-laced dress shoe, while a brogue is any shoe that features decorative perforations called broguing. Technically, an Oxford can then also be a brogue.
What Counts as Formal Shoes?
Formal shoes and dress shoes are the same thing. However, some dress shoes are more formal than others. Oxfords are more formal than derbies, while loafers are considered a more casual dress shoe. However, since loafers come in many styles, some loafers are also more formal than others.
To traditionalists, formal shoes are those specifically meant for formal events such as opera pumps and patent leather Oxfords.
In short, what is a “formal shoe” depends on who you ask.
What’s the Difference Between a Derby and an Oxford?
Oxfords have a closed lacing system, while derbies have an open lacing system. This means that derby shoes have the eyelet stitched on top of the vamp instead of into them like with an Oxford. Derby shoes are more topographical and less formal looking.
Conclusion: A Dress Shoe for All Personal Styles
If you’re more traditional, an Oxford or even certain loafers are probably more your speed.
Maybe you don’t even like formalwear, and you’re a workwear kind of guy. Sneak in some hardware to your suit-and-tie occasions with some monk straps.
It’s interesting how basically every dressy item in our arsenal evolved from functional ancestors. Heck, in ancient Greece and Rome, sandals were considered formal shoes since most people went barefoot.
Meanwhile, the Oxford was originally a rebellious piece of casual footwear. Now, it’s the go-to textbook dress shoe.
What’s your favorite type of dress shoe? Loafers? Opera pumps? Let me know in the comments!
