Men’s Stylish Dress Shoes

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Having an excellent pair of dress shoes is a necessity for most men, even if they typically work blue-collar jobs or rarely go out. Even men who love to wear hoodies, jeans, and sneakers are going to have to wear a suit occasionally, so it pays to be prepared and have the right items. That brings us to men’s stylish dress shoes, what types are available, as well as how to pick the right ones.

This guide is going to help you make the best choice for your new men's dress shoes. Once you understand what options and types are available, you'll be ready to find the right pair necessary for any special event, including weddings.

Anatomy of a Dress Shoe

Before we talk about the slight variances of style, you first need to understand all the components that make up your dress shoe.

Dress Shoe Parts

From the front to the back, a dress shoe has four parts: the toe, facing, quarter, and vamp (not necessarily in that order). The construction and placement of these four parts determine the individuality, style, and design of the dress shoe.

The toe is the part that covers your toes, while the vamp is the part of the shoe covering the top of your foot. The facing is the part just above the vamp, which holds the laces and is in the center of the foot while the quarter is the side of the shoe toward the back housing the heel.

Of course, within those four components, you have others, such as eyelets for laces and a tongue to hide the sock and provide a sturdy base for the laces. You also have the lining, which can be a variety of materials. The shank or waist of the shoe is the part between the outer edge of the vamp and the heel, and the topline is the uppermost part of the shoe in the very center of the back (ankle).

A Note About Closed vs. Open Lacing

It's important to note that some shoe styles, the Derby and Oxford, in particular, have specific lacing styles. The Oxford is always a closed lace while the Derby’s are always open laced.

Closed lacing means that the facing and quarters are secured underneath the vamp. It provides a less flexible fit, but you get a more formal look.

The open lacing, on the other hand, has quarters sewn to the top of the vamp, allowing the facing to flap open near the tongue. You get a more flexible fit, but the look is slightly informal. They both look so similar, though, that most people cannot tell the difference.

Types of Men's Dress Shoes

Now that you understand the anatomy of a dress shoe for men, it's essential to learn a few of the basic styles and options. This way, you can make a more informed decision.

You’ll also learn about the variances within each style. For example, an Oxford can have a variety of different stitching and styling, but the basic shape and fit stay the same.

Oxford Shoes

The Oxford is also frequently called the Balmoral. You can find cap-toe, whole-cut, wingtip, and plain-toe Oxford styles.

These are one of the most timeless and basic dress shoes on the market, and they’re the perfect starting point for men who have no idea what dress shoe to purchase. Men's Oxford shoes are highly versatile so that you can dress it up and down for daily or formal wear outfits.

  • History

These shoes became highly popular in the 1800s among college students, primarily students from Oxford University. The style was high-ankle, and during the turn of the century, students desired something more low-cut for the shoe because the half-boot style of traditional Oxfords was outdated by that time.

  • How to Identify Them

If you’re walking down the street, you can easily see the Oxford when it presents itself on the foot of a well-dressed man.

The most recognized trait of the Oxford shoe is the closed lacing, which means that the facing of the shoe is attached under the vamp. This allows you to have a slimmer silhouette, which hugs your foot’s contour and gives a streamlined look.

  • How to Wear It

Oxfords are primarily popular because they have a minimalistic look, and they go well with any outfit (including the jeans-and-blazer look). You can find a variety of colors for everyday wear, including blues, browns, greens, and reds. You can also find suede and leather varieties.

If you want the shoe for business attire, you should probably go with black, English tan, Cordovan, or dark brown leather options. These are considered safe to wear with any outfit, though you should try to match the shoe to the outfit. While the battle rages on for wearing black and brown shoes together, we tend to think that this fashion statement is a little too bold for the workplace.

If you plan to wear Oxfords with a tuxedo (and you very well can!), it is best to choose black patent leather because it is going to be shiny and look more formal than other options.

The One-Piece Oxford

While mentioned briefly earlier, it’s important to understand the one-piece Oxford and how it differs from other options. It’s a variation of the timeless classic because it's constructed of one piece of leather rather than multiple pieces that are sewn together. As such, it has one seam.

The limited stitching gives you a more sophisticated and sleek look, which adds to the no-nonsense, simple styling.

The Derby Shoe

The Derby style is frequently called the Blucher. It comes as a plain-toe, cap-toe, and wingtip, giving you the advantage of choosing the one which best fits your needs or style preferences. While it's highly similar to the Oxford, it does have a slightly more casual showing.

  • History

The Derby shoe has also been called the Gibson and the Blucher, and it was primarily a hunting and sporting pair of boots back in the 1850s. At the beginning of the 20th century, these shoes became popular for going into town.

  • How to Identify Them

Derbies are usually miscategorized as an Oxford because they have a similar shape and the differences are so subtle that many inexperienced salespeople can’t tell them apart. However, there is a key difference between the Oxford and the Derby.

The Derby shoe has the facing which is attached to the top of the vamp, which is called open lacing in the shoemaking world. This allows you to have a wider and more relaxed fit at the top of the foot.

The wider, more comfortable fit is synonymous with the sporting roots of the shoe and solidifies the position of the shoe as a casual alternative to the Oxford. With that being said, both shoes are appropriate to wear to formal events.

  • How to Wear Them

The best part of the Derby is that you can wear them just as you would the Oxford shoe. However, remember that the Derby style is slightly more casual, so you aren’t likely to wear them alongside a formal suit.

They work best with rolled jeans or the jeans-and-blazer look. You can also wear them well with Chinos and khaki-style pants.

Monk Strap Shoes

If you’re like most people, you’ve heard of Oxfords before and may have had a meeting or two with a Derby without realizing it. However, that's where most people’s knowledge of men’s stylish dress shoes evaporates.

The problem is that there are so many other amazing styles out there that you’re missing out on because you’re unaware that they exist. Take the Monk Strap, for example. You have a buckle and strap instead of laces, and you can choose between the single-strap or double-strap version.

If you’re looking for something that is slightly more formal than a Derby but not as formal as an Oxford, this laceless shoe fits the bill.

  • History

This shoe’s design gets its name from the monks, as they originally wore them. It has a closed-toe design which helps protect the feet and toes from rocks and other debris. They gave more protection than traditional sandals and were worn when the monks had to travel great distances.

  • How to Identify Them

The Monk Strap is quite similar in construction and shape to the Oxford, but it doesn’t have an eyelet closure. Instead, the Monk Strap uses a wide strip of leather, which is fastened across the front of the shoe.

The strap can be fastened with one or two buckles, depending on the style. Many people believe that the single-buckle version looks dressier than the two-buckle version, but we believe that's a matter of preference.

  • How to Wear Them

This alternative to a lace up dress shoe can add panache and a sense of uniqueness to any outfit as well as the person wearing them. The monk strap is regarded now as a highly versatile shoe; it can be worn with the most formal of suits or cuffed jeans.

They're designed to draw attention to the feet and the wearer, so you may find that your shoes become a focal point of your attire.

Many times, the monk strap shoe is made of suede or leather. Sometimes, it can have a decorative feature called brogueing, which is a pattern of punched holes along the shoe’s seam.

Men's Loafer Shoes

Most people have heard of loafers (think penny-loafers), but there are three styles available, including the bit and tassel loafer. Loafers are a moccasin-inspired shoe style that can be slipped on and off easily, adding to its appeal.

  • History

The original loafers were casual house slippers designed for King George VI of England. It wasn’t a popular style and wasn’t acknowledged until it made its way into the United States in the 1930s. Nonetheless, it still wasn’t as popular as it is today until the 1960s when American lawyers and businesspeople started wearing them with suits.

In 1966, the Gucci brand introduced the first horse bit loafer, which featured (and still features) a metal strap across the instep. This strap is in the shape of a horse bit.

The Gucci innovation led to the loafer slip on shoe being considered a more formal footwear option or at least helped to confirm that the loafer wasn’t only available for casual styles.

  • How to Identify Them

Loafers usually have a saddle or a decoration, which could be a strap that has a slit (as for penny loafers), a plain strap, or metal ornamentation. Tassels or kilties can hang from the saddle, as well. However, you can also find a minimalistic loafer called the Venetian, which exposes the vamp and doesn’t include any ornamentation or embellishment.

Loafers have a signature characteristic, especially when they look more like moccasins rather than slippers. The elevated seam runs across the toe, and it’s featured on almost every loafer out there.

Of course, you can also find a variation of them, called the driving shoe or driving moccasin. They’re usually made with softer materials and have less structuring. Along with such, the heels and soles are made for comfort when you’re driving.

  • How to Wear Them

You can wear Venetian and embellished loafers with suits in formal settings. Do note though that they aren’t usually considered dressy enough to wear with tuxedos and other formal wear. Nevertheless, you can choose to wear them with a variety of casual styles, including rolled jeans and khakis.

The goal here is to choose the shoe color based on the outfit. If you’re wearing a black outfit, even if color is added, you should choose black dress shoes. The same applies to navy blue suits and shoes, and brown or tan suits and shoes.

Dress Boots

The dress boot is something that most men shy away from because they’re worried about how dressy or formal it can be or how to wear it. It’s a short boot with a lace-up style. It’s constructed similarly as an Oxford, but it has a longer shaft.

  • History

The dress boot gets its roots from the Victorian age because men had few footwear choices. The dress boot became an acceptable option for formal daywear, and it's still an excellent alternative to the standard dress shoe of today.

  • How to Identify Them

Dress boots are constructed like Oxfords, and they usually have the same shape but a longer shaft. The lace-up boot is short and can feature wingtip brogueing along the seams and on the toe.

  • How to Wear Them

Again, most men don’t like wearing dress boots because they aren’t sure if it matches the overall style of the outfit and the event for which they’re attending. The question becomes, “When is a men's boot considered dressy enough to wear with a suit?”

The boot needs to be sleek and should have a slim appearance. The laces are likely to be thinner, and the sole should distinguish it as a high-top dress shoe.

In most cases, commando and lug soles aren’t appropriate, though these can be the exception that proves the rule in some cases.

If you choose fine leather boots, you can opt for brown or black or any of a variety of other colors; just make sure the color complements the suit. While styling experts can easily determine if suede is appropriate, it’s best to stick to leather dress boots instead of suede.

Opera Pump

While most men believe that a pump is for a woman, the Opera Pump is a shoe designed for men. It’s only to be worn with the most formal attire, such as that you’d wear to the opera or ballet. It’s one of the most formal dress shoes out there, and men also get worried about when to wear it.

  • History

These shoes were quite popular during the Victorian Era and were one of the essential parts of eveningwear attire. Men wore the pumps with breeches and knee-high stockings to dances, operas, and other events.

  • How to Identify Them

Opera pumps are a slip-on dress shoe and are usually made of patent leather. They're also traditionally adorned with grosgrain bows.

  • How to Wear Them

While opera pumps aren’t quite as popular today as in the past, opera shoes can still make an appearance, but only at full-dress events. If you’re an individual who likes fashion, you can choose to wear these shoes at ritzy parties while wearing a tuxedo or formal suit.


Choosing a pair of well-made dress shoes is essential. You know you’re going to wear them throughout your years, and the best part is your feet aren’t likely to grow or change much as you get older. Therefore, if you choose shoes that are well-made and high-quality, you can get many years (or decades) out of them.

Ideally, you should focus on choosing shoes that help you express your style and fits in with the men's clothing outfit you like to wear. You can add dimension and uniqueness to the shoe by adding colorful laces or learning about creative lacing options.

It's important to make sure that you can comfortably afford the men’s stylish dress shoes. You may not be able to spend a small fortune on them, but you can still get quality. If you only plan to wear them for weddings and funerals or the occasional formal business event, you can get a fashionable pair for yourself at a reasonable price.

Last Updated on December 19, 2021 by admin_comfortabledressshoes