12 Types of Dress Shoes Every Man Should Know About

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by  Jon Wadsworth | Last Updated: 
types of dress shoes

Just like there’s the right tool for every job, there’s the perfect dress shoe for every occasion. 

The problem is that there are so many dress shoes, it’s hard to know where to start.

Brogues, Oxfords, derby’s. The list goes on. Today, we’re getting our geek on and looking at the 12 types of dress shoes you need to know about.

12 Types of Dress Shoes for Men 

1. Loafers 

Contrary to what you might think, loafers can be worn as part of a casual look or with a suit. 

In fact, loafers were considered “business casual” as far back as the 60s. Designed initially as a slipper for King George VI, loafers grew in popularity thanks to the introduction of the Gucci Bit Loafer.

A classic-looking bit loafer like the Beckett Simonon Beaumont Loafer is a perfect example of a dress shoe that can be worn in any situation. A pair of loafers pair well with a suit and are incredibly comfortable to wear.

Beckett Simonon Beaumont Loafers

Made with full-grain leather, Beckett Simonon’s Beaumonts lean a touch casual thanks to the rounded moccasin-like toes and beefrolls. They offer the sophistication you want in horsebit loafers, but aren’t as intimidating for horsebit newbies as Guccis would be.

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While the Beaumont is an example of a bit loafer, you can also find tassel loafers, which can either have a tassel set into the vamp or a kiltie attached for added decoration. 

Many loafers also have a raised seam running along the toe, giving them a moccasin style. You can wear any style of loafer as a dress shoe, though for myself, the only style I would consider as a full dress shoe is the Venetian style, which I discuss further in the article. 

2. Monk Strap

So-called due to the resemblance to the types of sandals that monks wore in the 15th century, the monk strap dress shoe is anything but monk-like in its elegance. A monk strap shoe is commonly seen with either a single or double buckle; the shape is similar to an Oxford but with more embellishment.

Beckett Simonon Hoyt Monkstraps

Crafted from Italian full-grain leather and with a classically refined last, the Hoyt is an exceptional showcase of the double monk style.

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If you’ve never tried a pair before, I think you’ll be surprised at how well monk strap shoes handle any clothing style you care to choose. The Thursday Saint, a double buckle style, looks great with a smart suit but is equally stylish when paired with trousers or tapered jeans.

Thursday Saint

Goodyear welted and with a premium leather outsole, the Saint is one good looking double monk, holy references aside.

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Monk strap shoes can be pretty narrow, and the best versions usually feature either a Blake stitch or Goodyear welt construction.. 

Monk strap shoes should be comfortable and can last for years when cared for. The look isn’t for everyone, but if you’re a fan, you’ve got a pair of dress shoes that will never go out of fashion.

3. Derby 

I class the Derby dress shoe as the workhorse of the dress shoe world; it’s a bit less formal than an Oxford shoe but slightly more refined than a dress boot. 

You can wear a Derby dress shoe all day long, then slip into them for a formal weekend event, and never worry about looking stylish or feeling uncomfortable.

The main difference between a Derby and an Oxford is that a Derby shoe has open lacing, which allows for a wider fit. Derbies are a looser fit and are perfect for when you’ll be on your feet for long periods of time.

The Dunham Derbies, by Beckett Simonon, are open-laced, comfortable dress shoes that target those of us who want to look good but expect reliability and durability from our dress shoes. They look great in the suit you’re wearing all week and smart jeans for a more casual look.

Beckett Simonon Dunham Derbies

The Dunham Derbies by Beckett Simonon, are open-laced, comfortable dress shoes that target those of us who want to look good but expect reliability and durability from our dress shoes. They look great in the suit you’re wearing all week and smart jeans for a more casual look.

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The Italian leather only looks better with age, so you’ll be maturing alongside these smashing dress shoes. The Blake stitching is noticeably slim, and like most Derby shoes, they’re incredibly comfortable. 

4. Oxford 

If your dress shoe journey is just beginning, you won’t go wrong with a timeless pair of Oxford dress shoes. 

Oxfords have been popular since the 1800s and are the perfect dress shoe for everyday use. Your Oxford will go with any outfit and won’t look out of place at any venue.

Despite being a classic design, Oxfords have adapted well over the years, and you can find them crafted from various materials. Dainite or leather soles are low profile enough to maintain the minimalist shape, and there are also several material choices for the upper design.

The iconic Oxford, such as the Allen Edmonds Fifth Avenue Oxford, has everything you’d need in a dress shoe. The Oxford style of closed lacing means your shoes have a slim profile that’s great for formal or casual wear. 

Allen Edmonds Fifth Avenue Oxford

This classy Oxford has everything you need in a dress shoe. The Oxford style closed lacing means your shoes have a slim profile that’s versatile enough for formal or casual wear.

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The Fifth Avenue Oxford has what’s known as a cap toe style to it, which is understated without being extravagant. 

You can also find Oxfords with wingtips, broguing, and plain toe designs.

5. Penny Loafers 

The two most widely used style of loafer is the above-mentioned bit loafer and the classic penny loafer, which has a strap across the vamp with a hole in it, much like the slot in your piggy bank. 

The decorative strap across a penny loafer is purely for show, but many people prefer the penny loafer as it’s slightly more understated. A loafer such as the Randolph Penny Loafer is a superb option if you’re not a tassel or kiltie fan. 

Allen Edmonds Randolph Penny Loafer

If you appreciate traditional style in your Penny loafers, these may just be your new grail. Handcrafted in Wisconsin, the single layer soles give them a sleek profile and the leather lined interior makes for comfortable wearing. Yeah, they're really classy.

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A slimline leather sole will keep your loafers looking sharp and become even more comfortable the more you wear them. Loafers are easy to resole, durable, and remain a fashionable option for a smart-casual look.

While most, if not all, dress shoes have a rounded toe, the style can change depending on the shoe, and loafers often come with a split toe or apron toe design that’s very reminiscent of moccasins.

6. Brogues

In its truest sense, an Oxford and a derby dress shoe can also be a brogue if they have a decorative broguing pattern along their upper. 

The term brogue is a reference to the punched holes that decorate your shoes rather than the style itself.

What that means for you though is that if you’re a fan of the pattern, you can invariably find a style of shoe you love that also has broguing. 

Brogues often go hand in hand with wingtip style dress shoes; even dress boots can have both broguing and wingtips, such as the Thursday Boot Wingtip

Thursday Wingtip Boots

I love the brogueing detail on the Thursday Wingtips. They're also a delight to walk in with their supple and super comfortable glove leather interior. I'm a fan.

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The Wingtip, a full grain leather dress boot with a Goodyear welt, is probably better suited to smart-casual but is a comfortable and long-lasting dress boot that’s great for the office.

You can find many styles of brogue dress shoes, with varying degrees of broguing that determine the style, and ultimately, it’s all down to your personal preference.

From a full-brogue wingtip to a half–brogue that’s a bit more understated than a full-brogue, you can even find a longwing-brogue, where the brogued wing continues round to the heel of your shoe.

7. Wingtip

A wingtip dress shoe has a distinctive winged cap that sits prominently on the toe of your shoe and, similar to broguing, can be found on many styles of footwear. Anything from an Oxford to a boot can have a wingtip style, as you can see from the Dalton Wingtip from Allen Edmonds. 

Allen Edmonds Dalton Wingtip

The Dalton Wingtip is one classy looking pair of dress boots. They're handcrafted in Wisconsin with ultra premium European leather uppers so they ain't cheap, but boy do they sing on the feet.

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The most common wingtip style has a full brogue pattern embossed across the wingtip for a mature look. If wingtips are for you, you should be able to hunt down a wide range of dress shoes that have a look that suits your wardrobe. 

The Beckett Simonon Wright Austerity Oxford is a superb option if you prefer a wingtip without broguing. With the classic wingtip style across the toe but holding back from any decorative broguing, the Austerity is perfectly named. 

Beckett Simonon Wright Austerity Oxfords

This shoe is a superb option if you prefer a wingtip without broguing. With the classic wingtip style across the toe but holding back from any decorative broguing, the Austerity is perfectly named.

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I’m a massive fan of the Austerity in the black leather It’s a superb dress shoe for more formal occasions, without looking stuffy or out of date. 

To be fair, Oxfords will never go out of date, nor will black dress shoes, and the wingtip adds that little definition, making this a fantastic dress shoe.

8. Chukkas

Only some chukka boots are suitable as dress shoes, but a surprising number can pull off the smart-casual look. Thanks to boots such as the Thursday Scout boot, many chukkas have a slim ankle profile, so unlike a pair of clunky boots, they won’t bulk out your trouser leg. 

Thursday Scout Chukka

The Scout is Thursday's take on the Chukka, and boy, do they pull it off. Featuring studded rubber outsoles and a tasteful slim profile, they look fantastic in denim.

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Many chukka boots, including the Thursday’s Scout, come with a rubber sole, which is excellent for grip and durability but makes them look chunkier than those with a leather sole. 

If you’re planning on wearing chukka boots as a dress shoe, look for the lowest profile you can find; the sleeker the profile, the smarter your shoes will look. A perfect example of a sleek-looking chukka boot is the Allen Edmonds Williamsburg Ankle boot. Its lower profile leather sole and plain design make it a great option to consider. 

Allen Edmonds Williamsburg Ankle Boot
$445.00

If you’re planning on wearing chukka boots as a dress shoe, look for the lowest profile you can find; the sleeker the profile, the smarter your shoes will look. The Williamsburg is a perfect example. Its lower profile leather sole and plain design make it a great option to consider.

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04/19/2024 04:45 pm GMT

9. Chelsea

The Chelsea boot is a great style choice for a modern dress shoe; you’re adding comfort and durability to a style that suits everything from an office to a wedding. 

The Chelsea was made popular during the swinging 60s London scene and remains as popular a choice today as it did when the Beatles made this classic boot look, well, classic. Usually found in leather or suede, a good Chelsea boot is understated but highly versatile.

If it’s a formal occasion, black is the only way to go.

The R.M. Williams Yearling Chelsea is clean, robust, has an interesting heel, and is very comfortable. If you’re looking for a smart-casual look, the deep Chestnut brown leather is an excellent choice. 

R.M.Williams Yearling Chelsea Boots

This Chelsea from the mast famous downunder bootmaker, R.M.Williams is clean, robust, has an interesting heel, and is very comfortable. If you’re looking for a smart-casual look, the deep Chestnut brown leather is an excellent choice.

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Coming with a wide range of soles, including leather, rubber, or studded, you should be able to match up both style and function and have a superb pair of boots. The Beckett Simonon Bolton Chelsea boot feels like you’re wearing slippers. Ridiculously handsome leather slippers. 

Beckett Simonon Bolton Chelsea Boots

This boot feels like you’re wearing slippers. Ridiculously handsome leather slippers.

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10. Venetian Loafers

While I’ve touched on the penny loafer and the bit loafer being an excellent choice for a smart-casual dress shoe, the Venetian loafer has only one function: an elegant dress shoe. 

Unlike its close cousins, the Venetian is a dress shoe in every sense of the word, and as such, you’ll have to dress to match the part.

There are worse crimes than wearing jeans with a pair of Venetian loafers such as the Magnanni Madrid Venetian loafer; I just can’t think of any off the top of my head. 

Magnanni Madrid Venetian Loafer

Finely textured Italian nappa leather defines a clean-cut Spanish loafer built with smart arch support.

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You’ll not find a simpler or more elegant style of dress shoe than this. Just keep them away from your Chinos.

Many loafers can be found with an apron toe style, giving them a moccasin-like appearance. That’s great for the smart-casual look, but the Venetian loafer style avoids all of this; it’s a dress shoe free from clutter.

11. Wholecut Oxford

The wholecut style of an Oxford dress shoe has to have a section all of its own; it’s the most formal option for Oxfordes. Wholecuts look far superior to almost every other option available if it’s a black tie event.

Wholecut Oxfords are crafted from a single, premium section of leather and will often come with a leather sole and blake stitching for even sleeker lines. The Beckett Simonon Valencia Wholecut has a great profile and Blake stitching and will provide the comfort and serious durability you’d expect from a premium pair of dress shoes.

Beckett Simonon Valencia Wholecuts

Wholecuts are rare and highly prized for a reason; they are the most difficult shoes to make. Not only does the single piece of leather need to be perfect, it has to be supple and the fibers must align.

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If there’s one issue with choosing a Wholecut Oxford, it’s the price, which can be pretty high. What you get for the price is a superbly-crafted, iconic-looking dress shoe that will last for years. 

12. Opera Pump

You won’t be wearing Opera pumps to the Christmas party, and you’re unlikely to wear them to a wedding, but for the absolute most formal dress shoe around, it’s the Opera pump or nothing. 

The decadent-looking Velasca Martingala Opera Pump hums with sophistication, but unless you’re a frequent visitor to the opera or possibly due to win a Nobel prize, this style of dress shoe might be one to hold off from.

Velasca Martingala Opera Pump

The smooth leather pump designed by Fabio Attanasio for Velasca is a shoe of rare beauty that can carry you to other eras. The calf leather has undergone a glossy finish, obtained by spreading a uniform layer of dye and brushing it by hand.

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You might have seen similar designs on prom shoes, and while there’s undoubtedly a market for opera pumps, I just wanted to ensure you had all the information needed. There are smart dress shoes, and then there’s the ball gown and tiara level of dressing smart.

Anatomy of the Dress Shoe 

Welt 

Depending on the style of dress shoe you’ve purchased, you may have a Goodyear welt, Blake stitching, or even a cemented welt. 

Cemented Welt

If you’re after a great pair of dress shoes that will last for years, I strongly advise against buying a dress shoe that’s been cemented together.

For a start, a cemented shoe is almost impossible to repair. You’ll not easily find a cobbler willing to resole shoes that have been cemented. Cemented welts are cheaper and usually mass-produced, and as a shoe connoisseur, feel free to join me in turning our noses up at this method of construction.

Goodyear Welt

The classic Goodyear welt has seemingly been around forever and is one of the most popular and readily identifiable types of welt you can find. 

What a Goodyear welt will do is allow for much sturdier shoe construction and one that allows for easy resoling of any worn soles. Your shoes will keep out water more efficiently, and your shoes will be more hard-wearing thanks to the two-level stitching employed.

If the Goodyear welt has one drawback, it’s that it can be quite bulky, which doesn’t make it the ideal method when creating a slim-looking dress shoe. For all other shoe and boot construction, it’s probably the way to go, but for dress shoes, there’s a better alternative.

Blake Stitching 

You can hardly call Blake stitching the new kid on the block; it’s a method that’s been around since the 1850s, but it’s the perfect choice for a dress shoe. 

Rather than having a welt on your new dress shoes, Blake stitching allows for a more streamlined approach where the stitching is used to marry the upper to the insole and outsole. 

Blake stitching creates a much lower profile, looks fantastic, and complements the aesthetic of a dress shoe. A drawback to Blake stitching is that it’s not precisely water-repellant, and you’re limited to a certain number of resoles rather than the endless resoles a Goodyear welt can take.

Blake Rapid Welt

A Blake rapid welt is a combination of Blake stitching, but with an added midsole like you’d find with a Goodyear welt, which allows for Blake stitched shoes to be resoled with ease. 

The Blake stitching still attaches to the insole, but a midsole is added in this method. 

The midsole is then stitched to the outsole, creating a Blake stitching look with the benefit of being more water-resistant. Resoling is more straightforward, but you’re losing the slimline look again due to the Goodyear welt appearance around the edge.

Lacing

You’ve only really got two options when it comes to the style of lacing for your dress shoes; open lacing and closed lacing. Closed lacing is a more formal and less flexible style, but looks great on a dress shoe worn for special occasions.

Open lacing is undoubtedly an excellent option for a dress shoe but has the advantage of being a looser fit. Open lacing could be perfect for you if your feet are notoriously wide.

A good way to remember which type of lacing is to check out a pair of Oxford shoes; the lacing is always closed, while Derby dress shoes will have an open lacing system. 

The quarters (the section of your shoes where the eyelets are) are either snugly fitting in a closed lacing option, or there’s a gap between each quarter, in which case you’ve got open lacing.

Top Lift 

A top lift is the part of your heel that’s in direct contact with the floor and is attached to your heel to protect your shoe from damage. Having a top lift means it’s easy for a cobbler to simply swap out an old, worn top lift and replace it. 

You’ll need to keep an eye on the top lift of your shoes, as once the top lift has worn down and you’re damaging the heel of your shoe, you’ll find repairs are more costly. Most people walk with a slight gait which means one side of a top lift wears down quicker than another.

Your dress shoes need looking after, especially leather ones that will age and become better looking over time. A top lift will add that additional layer of damage control; be mindful that on a dress shoe, they can be thinner to maintain a shoe’s lower profile.

Vamp 

A vamp is the top of your dress shoe, situated between the toe box and the facing (where your laces sit), and should invariably be decoration-free. Any broguing that your dress shoes may have will be around the toe and, in the case of wingtips, down the side of your shoes. 

Dress shoes are sometimes close-fitting, and the vamp area could be tight if you’re wearing the wrong size. If you find your feet are aching on top after wearing your dress shoes for a while, the vamp may be too tight. Try wearing thinner socks; otherwise, you may have bought the wrong size.

6 Most Popular Dress Shoe Toe Styles 

Dress shoes come in many different styles, though the toe shape is usually a rounded shape. It’s not impossible to find a dress boot with a more tapered toe, but your dress shoe has a rounded toe for a more classic or traditional look.

The embellishments and styles available on the actual toe of your dress shoes can vary wildly, from the most basic to the more stylized. Your primary choices when it comes to toe styles are:

  • Plain toe
  • Wingtip
  • Split toe
  • Cap toe
  • Apron toe
  • Medallion

Plain Toe

A plain toe on your dress shoes can be the best choice available. You’re letting your shoes and clothing remain understated; you don’t need adornments to pull off the style you’re after. A plain toe, without stitching or broguing, should always be a part of your collection.

Wingtip Toe

With a wingtip style, your dress shoes have a winged cap that peaks right in the middle of the toe box. Many wingtip dress shoes also have broguing as a decoration covering much of the wingtip.

Split Toe

A split toe is easily identified by the vertical stitching that comes up from the front of the toe and extends all the way around your shoes to the middle of the heel.

Cap Toe

A cap toe style has a stitched line that reaches horizontally across the back of your toe box to cover an additional strip of leather placed over the toe box or as purely decorative stitching across the original vamp.

Apron Toe

An apron toe usually has a seam that runs around the top of the toe, almost encircling the entire vamp of your shoe. A common sight on moccasins, an apron toe often goes hand in hand with a split toe shoe.

As the split toe seam heads up the front of the toe box, it hits the apron toe seam and creates a T-shape before the apron seam heads around the edge of the vamp area of your shoe.

Medallion

Whereas a wingtip style toe may have broguing that extends along both sides of the vamp, a medallion toe is without the distinctive wings. Any broguing or decoration is reserved for the top of the toe. 

Imagine a medallion toe looks much the same as the hood of a Ferrari does with the rearing horse emblem right at the front of the hood, and you’re in the right ballpark.

Which Dress Shoes Should You Get?

Having someone else choose the dress shoe you should buy is as tricky as choosing who someone should marry. 

It’s all about your personal preference, style, and personality. I’m not a fan of wearing brightly colored trousers with outlandish socks with my dress shoes; the style just doesn’t suit me.

That’s not to say I don’t think it’s not a great look; I simply can’t pull it off; I look like a depressed clown. The dress shoes you choose should be a reflection of your personality and style, and perhaps just as importantly, where you’re going to be wearing them matters.

Rocking up to a job interview in a pair of opera pumps will certainly cause an impression, but they’re not the right tool for the job. 

I love dress boots, but only as a more casual look, perhaps for the office or for a weekend trip.

For formal occasions, consider Oxfords or brogues, as they add an air of maturity and sophistication to any outfit. But if you can pull off a pair of monk strap dress shoes with a pair of burgundy trousers and lime green socks, knock yourself out.

Your own style and the occasion matter, but finding a dress shoe that’s flexible enough for multiple situations can keep your wardrobe fresh and your feet happy.

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