Men's Dress Shoe Guide

June 07, 2018 9 min read

Men's Dress Shoe Guide

Nothing changes quite as comprehensively as fashion. Go back through time and examine the clothing through different decades — the waistcoats, the top hats, the hoop skirts and the outlandish wigs — and you'll soon be reminded how much things change. The only constant in fashion seems to be the human beings beneath the clothing.

There is one exception, though. Aside from some small details, the general look and feel of men's dress shoes have stayed the same.

It isn't hard to see why. Take a look at men's formal footwear from the 1800s and you won't notice a terrible number of differences from the shoes worn today. Men's dress shoes are like sharks — they evolved long ago and were so close to perfect that only minor improvements have changed them since.

In this article, we'll take a close look at what makes a man's dress shoe a man's dress shoe. We will examine the different parts of the shoe itself, what types of shoes there are to choose from, what clothes they pair with and the different materials available.


The Anatomy of a Men's Dress Shoe

The parts of a men's dress shoe provide a glimpse into the level of expertise and history that go into them. Note that some of the following items will not be present on certain dress shoes. The purpose of this list is to illustrate all the parts of a men's dress shoe that may appear on the shelves of a shoe store. This way, you will have the vocabulary to communicate what you want when asked.

Let's begin with the lower portion of a men's dress shoe:


  • Outsole: The outsole is the bottommost layer on the shoe's sole. This can be made from wood, rubber or a synthetic material, and is responsible for providing grip when walking.
  • Heel: Men's dress shoes have an elevated heel to lessen the angle of the foot to the leg. The heel also provides extra shock absorption when walking, while adding a bit to a person's height.
  • Shank: The shank is a piece of wood, fiberglass, metal or plastic that spans from the heel to the ball tread area of the shoe. It is roughly four inches long and around half an inch wide, and provides some spring that keeps the elevated heel from distorting the shape of the shoe. Not all shoes have a shank, as they are only required when the heel adds significant height to the back of the shoe.
  • Waist: This refers to the middle section of the lower shoe, where the edge of the heel meets the narrower portion before the ball tread.
  • Welt Stitching: The welt is that thin piece of material at the intersection of the upper and lower shoe. Welt stitching is what connects the upper and lower shoe, and the quality of the stitching is extremely important in the longevity of the shoe. The welt also plays a role in keeping water out when walking on rainy days.


Now, let's move to the upper part of a men's dress shoe. This includes everything above the welt:


    • Quarter: Moving from back to front on the main body of many dress shoes, you'll notice three different sections of leather. The rearmost section is known as the quarter. This is a complex part of the shoe — it extends to encompass the area under the laces, occasionally wrapping around the entire backside of the shoe and at other times reaching up to form a collar around the top line. What role the quarter plays depends on the style of shoe.
    • Vamp: The vamp is the middle section of leather on a shoe between the toe and quarter. Occasionally, the vamp will reappear from under the quarter and form the curve around the heel of the shoe, but often the quarter takes up the whole backside. Sometimes the vamp is stitched together from several different pieces of material for aesthetic quality, though it is commonly made from a single piece. The vamp also forms the underlying tongue that extends up under the laces.
    • Toe Cap: Some shoes feature a toe cap, or a separate piece of material covering the toe of the shoe. These may be stitched over or may completely replace the superior aspect of the vamp.
    • Toe Box: A toe box is a structural component of the toe cap, which forms a curve over the toes and provides a type of roof. This part of the shoe also maintains the shape of the rest of the shoe while allowing for movement in the toes.

Description of a Toe Box

  • Throat: At the bottom of the lacing area is the throat, where the frontmost part of the quarter is stitched onto the rear of the vamp. Sometimes referred to as the throat line, the position of this area also determines how much room the foot has to enter the shoe. A lower throat means more room.
  • Eyelets: These are the holes through which laces are strung, and they are often reinforced with grommets to prevent the string from tearing the material.
  • Tongue: This portion of the vamp extends up under the laces, forming a continuously sealed surface under the laces instead of exposing the top of the foot.
  • Facing: Facing refers to the upper portion of the quarter, around the laces, that is facing forward as one walks.
  • Lining: Inside the shoe, a lining may be present to provide comfort, warmth and moisture absorption.
  • Top Line: This is the rim around the top of the shoe.

Types of Shoes

Different types of men's shoe styles are appropriate for different occasions and levels of formality. Here, we will rank shoes from most formal to most casual, with suggestions on what to wear them with:

1. Cap Toe/Wholecut Oxford and What to Wear It With

Before we begin discussing a cap toe or wholecut Oxford, it is worth describing what an Oxford actually is. This style of dress shoe has eyelet flaps that contain stitching at the point where they connect with the vamp. This way, they are able to connect on the same plane as the vamp.

The wholecut Oxford is the upper echelon of formality in a men's dress shoe. Essentially, it is an Oxford shoe that has little to no perforation, extraneous stitching or superfluous design. As such, its upper section is made from a single piece of leather. Whereas other shoes are sewn together like quilts, a wholecut — now the name makes a bit more sense — is much like a blanket, made from a single piece of material.

A cap toe Oxford also has closed lacing, though it may feature a couple lines of stitching on the front of the shoe for modest style. This creates the impression of a toe cap. Either way, it is still a simple shoe and is quite dressy.

Wear this shoe with blazers, sports coats and wool trousers. It is also the shoe of choice for tuxedos, cotton dress pants that are pressed and well-fitting, and a shirt and tie type of affair.

2. Semi-Brogue Oxford and What to Wear It With

There is some fascinating history behind this shoe, with its many decorative holes and perforations. Once long ago, this was the shoe of choice for those needing to traverse boggy, wet fields. The holes were there to let the water and muddy goo escape.

In a bizarre turn of fate, it has become one of the most fashionable, dressy shoes in existence. These shoes have a perforated cap-toe, different leather layers and lots of decorative holes. They have closed lacing, meaning the facing and quarter are underneath the vamp, which makes them formal. Compared with wholecut Oxfords, these semi-brogue Oxfords are slightly less dressy but far flashier.

These shoes can be worn with most suits, blazers and sports coats with wool pants, or even dark jeans provided the shoe is the right color.

3. Wingtip Oxford and What to Wear It With

With wingtip Oxfords, the difference lies in the toe portion of the quarter. Whereas the semi-brogue Oxford features a relatively conservative quarter termination on the vamp, the wingtip Oxford's toe sweeps into a characteristic "M" shape. The closed-lacing of the Oxfords is easier to lace up than open-laced counterparts, and are excellent for semi-formal occasions.

There is some debate as to what these shoes should be worn with. Some believe they fit well with suits, while others disagree — however, it is a common practice and tends to look wonderful. They match nicely with wool or cotton pressed pants, or can look at home at a laid-back gathering with dark jeans and a sports jacket.

Wingtip Oxford Shoe

4. Cap Toe or Plain Derby and What to Wear It With

This is the first departure from Oxfords on our list, and now we enter the world of derbies. Derbies feature open laces, meaning the quarters are attached to the top of the vamp and can flap open. This makes them less formal than Oxfords, though they are more common and extremely versatile.

A cap toe or plain derby has eyelet flaps that are sewn onto the shoe's upper substrate. This makes them less dressy because they are slightly less sleek — the stitching interrupts the smoothness that might be common in Oxfords. However, it is worth noting that many manufacturers refer to their derbies as Oxfords.

As for what derbies can be worn with, the list is long. Technically, a derby shouldn't be worn with a suit — however, most men do wear derbies with suits. The result, shockingly, is that no one minds. These shoes look excellent and, despite their lack of closed lacing, can still pull off a stylish coup with suits. Penner's Stacy Adams collection has many variations of this type of shoe, as well as others.

If you do wear derbies with a suit, try to wear shoes with slim soles and a good polish. They look especially good with cotton, tweed, linen or other casual suits, as well as wool, cotton or denim pants.

5. Single Monk Strap and What to Wear It With

Harkening back to the days of old and yet sporting a quasi-modernist flair, the single monk strap dress shoe relies on a single buckle to provide tension instead of a set of laces. These are reminiscent of Colonial pilgrim shoes, in a way, except that the buckle now resides more to the side of the shoe rather than on the top.

These shoes emerged several years ago as a somewhat edgy trend in shoewear, but they seem to have stuck. Due to their simplicity, they can actually pull off significant sleekness. Just as an Oxford shoe is dressier due to its simpler profile and silhouette, the single monk strap can attain a unique elegance due to its design.

Single Monk Strap Oxford Shoe

For now, single monk strap shoes are good for informal suit occasions. If you are wearing a suit with no tie, wool or cotton pants and/or chinos, the single monk strap shoe can look great. You can find some suede versions of this shoe that look excellent with jeans as well.

6. Double Monk Strap and What to Wear It With

Single monk straps have a single wrap close to the top line of the shoe. The double monk strap features an extra buckle towards the front end of the shoe. Many people don't know what to make of these shoes, and the reason for this is that they are rather edgy in terms of fashion. However, they are quite elegant and are a great choice for putting together an outfit that is both classic and trendy.

Try the double monk strap with suits, but know your audience. If you are attending a gathering with more conservative dressers, or if the mood is somber, the double monk strap may be a bit too much of a statement. They work well with wool, denim or cotton pressed trousers.

7. Semi-Brogue Derby and What to Wear It With

A surprisingly rare shoe is the semi-brogue derby, which is much like the semi-brogue Oxford except for its lack of closed lacing. This shoe features flaps for lacing and eyelets, along with many decorative holes and perforations in the leather. This means the shoe has a lot of visual busyness, making it great for informal occasions but not for formal ones.

Try this shoe with wool, cotton or denim pants. If you are brave, you can experiment with pairing them with a suit, though be aware of how much disproportionate attention they can draw away from the rest of you.

8. Longwing Derby and What to Wear It With

This is simply a wingtip shoe, except the wingtip wraps around the entire shoe — all the way around the heel. This is a really versatile piece of footwear. The long wing around the shoe creates a sporting feel that is great for livelier atmospheres.

Wear this shoe with any type of casual clothing. Try suede shoes for even more options and versatility. Many types of summer clothing will likely match well with a longwing derby.

9. Suede Bucks and What to Wear Them With

Last but not least are suede bucks, which are a derby-style shoe with a plain toe and very little in the way of decorative stitching or perforations. They are often made from suede or nubuck.

Try wearing this shoe with anything summery. Darker shoes match with chinos, denim and cords, while gray shoes can match with virtually anything.


Come See Penner's Extensive Collection of Men's Shoes

Penner's has a long history of leading the way in the world of shoes. From our beginnings in 1916 to our current position as one of the country's most dedicated shoe outlets, our passion for shoes has never diminished. Our store in downtown San Antonio, Texas, features more than 8,000 square feet of retail space, seven in-house tailors ready to perform complimentary alterations and an unparalleled staff.

Penner's Has a Wide Variety of Men's Dress Shoes

If you want to spice up your wardrobe with a new suit or sports coat or are interested in choosing the right shoe, head over to our website and take a look at the many options we have available. Contact us with questions here or call us at 210-226-2487 before ordering online.