Men Style

A Man’s Guide to Boots and Shoes

A Man’s Guide to Boots and Shoes

Over 70 years ago, archeologist Luther Cressman discovered perhaps the world’s oldest footwear in Central Oregon. The sandals were dated to be 10,000 years old, were made with intricate weaves that indicated they were not only functional but also stylish in design. From our tribal days to modern times, men have searched for and valued footwear that both looked good and got the job done.

Quality dress shoes that fit well are a worthy investment. The right shoes for the occasion can substantially elevate your personal style and comfort.

Why care about your shoes?

A man should care about his footwear if for no other reason than it is the very foundation he stands upon. On an average day, your shoes will absorb the force of your weight 3000+ times; a poor choice here can lead to not only discomfort but injury.

Then there is the appearance aspect. Shoes are a visual endpoint and receive a disproportional amount of attention; despite covering only 5% of your body they can make-up more than 30% of the visual judgments we make when sizing up a stranger.

Ideally, you want to choose footwear that is both functional and stylish–by following these footwear selection principles this goal can be easily achieved.

Four Footwear Rules

 1- Wear the right shoe for the occasion –

this is the most common mistake men make when it comes to footwear. Wearing shoes outside their prescribed function is fine as long as they are still appropriate.

2- Invest in quality 

Not every man can afford to spend hundreds of dollars on his shoes. However, low-quality footwear constructed of cheap raw materials that do not age well; you will save money long term by buying more expensive shoes that will last longer. In order to buy quality, many men will have to save and budget for the purchase.

This can instill a respect for the quality of the product and encourage you to take better care of them. Assuming you can find a pair of quality shoes that fit you well, you can send them back and take advantage of their re-crafting and re-soling service – a new pair of shoes for a fraction of the cost.

3- Never sacrifice proper fit and comfort 

buy the right shoe size, even if this means paying a bit more and purchasing your shoes at a real store vs. the lowest price online.

Pay attention to shoe width. Men with extremely wide or narrow feet learn about this early in life. Look for variations in arch support and toe structure as well

4- Take care of your shoes –

Learn how to waterproof your shoes and then learn how to shine your shoes. In addition, rotate through a few pairs to allow them to dry between wearing and ALWAYS use wood shoetrees that will quickly soak up perspiration. This is especially important for leather shoes, as the interior of a dress shoe has often not gone through the harsh chemical treatment of the upper and is more susceptible to rot.

Common Footwear Terminology


commonly referred to as the bottom part of the shoe or boot and can be further divided into the outer sole, mid-sole, and insole depending on the type and quality of the shoe being discussed.


A general term that refers to the part of the shoe above the sole


a form of ornamentation in which tiny holes are carved into the shoe’s leather

An important point to remember is that the more decoration on a shoe the less formal it becomes.

Open Lacing

One of the two lacing systems used in oxford shoes; the open lacing system delineates the shoe in question to be a blucher. The shoe’s tongue and vamp (parts of the upper that cover the top of the foot); are cut in one piece with an open throat.


As mentioned above, a subsection of the general term sole; the inner sole is the layer of the sole upon which the footrests. A quality insole can mean the difference between a shoe that will last 5 years and one that will last 25.


The back portion of the shoe comes into direct contact with the ground and gives elevation to the foot; when the shoe is worn

Heels often built from 2 to 4 pieces of leather called lifts and reinforced with rubber or metal.


The choice usually round or ribbon; with round having the advantage of being stronger and more formal; thanks to their core while ribbon laces come in a variety of colors and are more elastic; making them a good choice for athletic shoes or hiking boots.

Men’s Footwear Types

Types Of Dress Shoes

Oxfords are lace-up shoes built to be worn below a man’s ankle.  They are commonly divided into balmorals and bluchers due to the difference in their lacing systems.  Balmorals are commonly referred to simply as “oxfords,” while bluchers are referred to as Derbys but rarely oxfords; all of this leads to confusion naturally.

Balmoral oxfords use a closed lacing system and are normally styled more simply than bluchers.  Thus balmoral oxfords are classified as the dressier of the two; they are best worn with suits and formal wear.  Every man should own a classic pair of balmoral oxfords to wear with his 2-piece suit.

Blucher’s derby shoes usually come in a much wider range of styles and colors; a conservative pair can be worn with a suit. And for many men is their go-to pair of shoes to wear with the suits in their wardrobe.  That being said, bluchers derby that utilizes brogueing, a split toe, or color combinations look best with more casual clothing.

Slip-on is not oxfords as they do not use laces; by design, they are less formal although if conservatively styled they can and have been worn with suits. However, they are generally more at home with grey flannel trousers and a sports jacket.   Moccasins, monk straps, and tassel loafers are just a few of the more popular options available.  Many of the styles you’ll find in the slip-on category could have been classified below as casual footwear; this just highlights the fact that there are very few hard lines when dividing items like this.

Click here for a more in-depth overview of the best men’s dress shoes.

Types Of Casual Footwear

Saddle Shoes

A casual oxford shoe, the saddle shoe is distinctive because it utilizes a layer of leather over the instep that is normally a different color than the rest of the shoe, thus classifying it as a casual but stylish choice.

Boat Shoes or Top-Siders 

Made to be worn on a boat to prevent slipping; they have migrated from the docks of Boston to the wardrobes of men looking for a summer shoe that can be worn without socks. Available in a variety of colors, the men’s boat shoe comes in a moccasin style and is only for warm weather.

Leather Laced – Heavy Sole 

The two most well-known shoes in this category are Dr. Martens and Sketchers.  Ranging from $40 to $200, these shoes vary in their build quality but are consistently casual in nature due to their large rubber soles and overall heavy appearance.  Relying on glue and being manufactured with shoddy materials. These shoes fill a niche but are not long term value pieces and are best avoided by a man looking to build a serious wardrobe.  I would say their one redeeming quality is their ability to withstand poor weather conditions, but if that’s your goal, then you should consider a quality pair of boots.

Canvas Shoes

Sneakers come in a wide variety of styles and colors, however, the rules of wearing them outside of the gym are universal.  When clean and situation appropriate, they work well with chinos, jeans, and shorts.

Leather Loafer 

separate from the slip-on leather dress loafers above; these slip-on loafers built with heavier rubber soles and more casual uppers to include leather imitations.  Their styles are wide and range, but the purpose of their construction is to fill the void between canvas shoes and dress shoes while maximizing comfort at a value price.  In the US the manufacturer Clark does an admirable job putting out a solid shoe; outside the US, look for Ecco and their wide range of casual and comfortable footwear.


One of man’s earliest forms of footwear, sandals continues to serve as a solid choice for protecting the bottom of our feet while allowing maximum air circulation to the upper portion.

Athletic Shoes

Running shoes, basketball shoes, tennis shoes–you would think the occasions for which these meant to be worn would be clear.  Yet we persist in wearing our white trainers everywhere, declaring it a right because they are comfortable.  I counter this argument by saying that many of us are too lazy to take the time to think outside the box and select a casual shoe that looks sharp and is comfortable. They definitely exist.

Types Of Boots

Work Boots

There are two types of footwear; high-end dress shoes that need to be conditioned and shined, and work boots that have gone through a beating and need new soles.  Quality work boots last forever and help you get the job done. Any man that works 14 hour days in construction learns at an early age that spending a bit more for quality boots is an investment in how his body will feel that weekend.  And as mentioned before, solidly built work boots can be re-soled, while cheap boots that are made with glue and inferior materials; not only fail under heavy usage but cannot be fixed as they designed to be disposable.

Hiking Boots

Hiking boots designed to support the ankles; provide cushion, and protect from the elements, while still being light enough to not impede stamina.  Boots that meet all these criteria are an outdoorsman’s delight; those that fail can turn a trip into a painful lesson of why quality matters.

Western Boots

Growing up in West Texas.  Functionally, they serve the purpose of keeping a man in his saddle; protecting him from the terrain, and if taken care of, they can last as long as his horse.  But that’s the issue–most of us don’t require this functionality and wrestle with the issue of whether or not we deserve to wear something so idealized by our culture.

A man can pull off western boots without being a cowboy – the key is being comfortable and confident in them.  And avoid flashy or brightly colored boots unless they have a special meaning or you crafted them yourself, otherwise, you’ll look like a clown.

Dress Boots 

This includes a wide variety of styles and manufacturers; from Red Wing’s Heritage collection to the classic Chelsea made famous by the Beatles.  While many built to withstand the rigors of hiking and working; dress boots are more often than not worn for their style, not their function.

A Note on Custom Made Shoes

All shoes used to be custom; mass-manufactured footwear that’s comfortable is a modern luxury.  Crafted one at a time, a man’s status (much more than today) determined by what he could afford to wear on his feet.   Today the art of hand-making footwear rests with a small number of artisans scattered across the globe.

First, when commissioning a pair of bespoke shoes be prepared to pay.  Handcrafted shoes are expensive because modern artisans only use the finest materials; there are very few of them that do this type of work, and it’s very time-intensive.  And believe it or not, demand is incredibly high–waitlists of 2 to 3 years are not uncommon.

Once the process begins, a bespoke shoemaker will first carefully examine your foot.  He’ll consult with you on the best style and design for your body and professional needs, then build lasts (replicas of your feet) which the shoe will be built around.

After this, the artisan performs his magic.  He’ll carefully select the right materials and then cut the insole, prepare the upper; prepare and then stitch the welt, sole the shoe, attach the cork filling and insert a steel shank spring; stitch on the outsole, build the heel, and then finish everything with final shaping and ornamentation.

General Rules for Men’s Shoes

  • Try to pick a shoe that matches, or is darker than your pants.
  • Socks do not need to match your shoes. Instead, think of your socks as you would a tie – items that can bring the whole outfit together.
  • If wearing a belt, try to match your shoes to it, unless of course, your belt is some multi-colored striped thing.

Men’s Shoes for Jeans

You can wear almost any color or style of shoes to wear with jeans. But avoid very shiny shoes that obviously intended for dressier outfits.

Boots, lug soles, sneakers, loafers, and sandals all these shoes work great with jeans. So you may find it helpful to let the style of your shirt guide you.

For example, a sporty, polo shirt might work with a loafer; t-shirts go well with sneakers or retro-style shoes; long, artsy button-downs work well with sandals or contemporary styles.

Man’s Guide to Boots and Shoes for Casual Pants

Whether you call them Dockers, chino pants, or khakis! there are a variety of loafers, oxford, and other men’s shoes that work well with casual pants.

Let the ornamentation and style of the shoe guide you towards the look you’re trying to achieve.

For example, a tassel or a buckle is a little more on the dressy side.  While a woven pattern or heavy stitching is a little more on the casual side.

Man’s Guide to Boots and Shoes for Dress Pants

With dress pants, shoot for the same type of shoe that you might wear with a suit. Shinier materials usually indicate a dressier shoe, as do less bulky heels and soles. Choose a shoe that is the same color or darker than your pants; and if wearing a belt, match your shoes to it.

Related: What Color Shoes To Wear With Your Suit

Color Matching for Men’s Shoes

  • Black shoes work well with navy, grey, or black pants.
  • Brown shoes are best suited to tan, brown, beige, greens, other darker earth tones.
  • Burgundy shoes work well with khaki, lighter browns, blue, and grey.
  • Tan shoes look great with lighter earth tones, blue, beige, lighter tan, or white.