10 Shoes Every Man Should Own | Essential Men's Footwear (2024)

Just like a sports car doesn't perform well with sub-standard tires, nothing kills your outfit quite like the wrong pair of shoes.

Every outfit calls for specific shoe styles and colors that elevate the entire look, or if ignored, can throw your complete look off. This kind of problem can also destroy your confidence.

Gents, it's time to upgrade your shoe game. In this article, I give you the 10 shoes every man should own by the time he's 30 and give you a little bit of history on them as well.

1. Cap-Toe Balmoral Oxfords
2. Tennis Shoes/Sneakers
3. Wing-Tip Brogues Shoes
4. Chukka Boots
5. Double-Monk Strap Shoes
6. Penny Loafers
7. Whole-Cut Oxfords
8. Chelsea Boots
9. Espadrilles
10. Boat Shoes

Shoes Every Man Should Own #1: Cap-Toe Balmoral Oxfords

Oxford's origins remain a mystery. Some believe that students of Oxford University in 1825 began wearing a style close to an Oxford shoe. Others claim that the Oxford shoe had origins in Scotland and Ireland; however, some have debunked this theory.

Nevertheless – the Oxford shoe is the most popular dress shoe today.

All Oxfords feature a closed lacing system, which can distinguish an Oxford shoe from a Derby shoe. A good quality Oxford shoe is made with box-calf leather and should not have any broguing.

An Oxford is a highly versatile dress shoe for job interviews, weddings, and black-tie events and can get you through almost any dress occasion.

A standard of menswear, the “Cap-Toe” Oxford, can be used in most professional situations. It distinguishes itself by the extra piece of leather added across the toe box.

Definitely one of the best examples of shoes every man should own!

Shoes Every Man Should Own #2: Tennis Shoes/Sneakers

When it comes to shoes every man should own, these are the ones most often done incorrectly.

Tracing its roots back to the 19th century and the Industrial Revolution, tennis shoes or sneakers have been around a long, long time.

Tennis shoes made their debut with canvas and vulcanized rubber. They served as a cheaper option to the hand-made footwear of the time.

Established in 1916, Keds made the first commercially available tennis shoes afforded for the general public.

Another shoemaker named Adi Dassler began producing sneakers in his home as a hobby. As his hobby grew into a business, Dassler formed the company known today as Adidas.

By the 1950s, tennis shoes became a staple in almost all children's and young adult's wardrobes. James Dean also helped this trend as he famously wore many different pairs of Converse low-top tennis shoes.

Today, Sneakers are everywhere, and some would say worn too much. I recommend owning a classic pair of low-top sneakers with a leather or suede upper.

Shoes Every Man Should Own #3: Wing-Tip Brogues Shoes

At the turn of the 20th century, Irish workers wore Brogues for outdoor work.
Interestingly, the broguing patterns we see on Brogues today that make them so distinct had a practical purpose.

Workers punched the holes through the shoes. The shoes drained water quickly that would catch in them without taking them off, saving time and money while the workers were on the job.

Elegant versions were worn by many, including actors and entertainers.

By this point, the perforations were used for style and were similar to what we see on Brogues today.

Brogues took off popularity in the United States, and famous actors like Cary Grant and Fred Astaire helped usher in a new Brogue era.

There are many different types of brogues, but we would recommend going with a “Full Brogue” or “Wingtip,” as shown above. They will likely be one of your most often worn shoes, making them an easy choice for shoes every man should own.

This will work well with slightly more casual dress/work options.

Due to the nature of Brogues, be careful to clean them often. The holes perforated in the shoes can fill up very quickly with dirt and dust.

I did the ultimate guide on how to clean, condition, and polish your dress shoes. Check out my shoe polish guide!

Shoes Every Man Should Own #4: Chukka Boots

With a strong sport and military history, chukka boots have become very popular and are a prime example of shoes every man should own.

Initially worn by the British Army in the desert during World War II, this iconic boot got the nickname of “desert boot.”

Coming in a variety of styles, a proper chukka boot must have a few distinct features. These include the top of the shoe hitting at the ankle, two or three eyelets, and a rounded toe-box.

Chukka boots also feature a distinctive two-part style from a single piece of leather, a shoe with the “folding over” effect on the top of the boot where the laces come together.
Chukka boots typically are unlined and have a leather or crepe sole.

Many famous men have worn this boot, including Marlon Brando, Steve McQueen, Jack Nicholson, David Beckham, Anthony Bourdain, Daniel Craig, Zack Efron, and Idris Alba name a few.

I recommend a suede chukka boot in a dark color such as brown or navy. But any chukka qualifies as a shoe every man should own

You can get a standard leather sole or a crepe sole. While the crepe sole is more comfortable than the leather, I still recommend the leather sole as it will last much longer.

A crepe sole can quickly deteriorate because of its coagulated latex that is very flexible but not durable.

Shoes Every Man Should Own #5: Double-Monk Strap Shoes

The origins of Monk Strap shoes are as mysterious as that of the Oxford dress shoes. Some believe that the original roots come from monks in the Swiss Alps who created a sandal that looked much like a monk strap shoe in the 15th century.

An Englishman later adopted this traveling and took it back to England. However, this has not been confirmed or proven.

Monk Strap shoes began to pop in England's early 1900s and quickly became an integral part of men's dress shoes.

While the Single-Monk Strap is the original Monk Strap, I recommend the Double-Monk Strap for most men.

The two straps are a more modern interpretation of this classic shoe and make the shoe look more balanced overall.

Double-Monk Straps also set you apart from most other men as they have a niche following and will catch people's eyes.

You can flex a lot of your creativity with these as you can get different types of buckles with many different buckle placements.

Shoes Every Man Should Own #6: Penny Loafers

With Norwegian roots, the first Loafer came about in 1936.

Fishermen in Northern Europe in the 1930s wore a slip-on style shoe similar to that of a moccasin. These early Loafers caught the eye of many men, and they began to transition their way into everyday casual wear when not wearing boots.

The Penny Loafer was developed years later and became the gold standard of Loafers even to this day.

The difference between a Loafer and a Penny Loafer is that a Penny Loafer has a shape cut out of the top of the shoe, creating a small pocket or slot in the shoe.

Penny Loafers are more relaxed than other dress shoes.

Loafers are not first on most guy's lists when they think of shoes every man should own, but they will help to add a bit of flair to your summer suit style. You should wear lighter-colored suits such as cream or blue in the summer months and not a black or charcoal suit.

Shoes Every Man Should Own #7: Whole-Cut Oxfords

The second Oxford to appear on this list, a Whole-Cut Oxford, is another shoe you should own by the time you are 30.

The Whole-Cut Oxford dress shoe has become increasingly popular in the last few years. It features a simple, elegant design constructed from one piece of flawless leather without a back-seam. It is understated and elegant.

Being constructed of one piece of leather, a Whole-Cut is unique from any other dress shoe and is the most delicate.

In addition to this, the leather must be of very high quality to stand up to the demanding manufacturing process. For these reasons, Whole-Cuts are generally produced by higher-end shoe manufacturers.

The Whole-Cut Oxford also features a ‘closed lace system,' which means the shoelaces attach under the vamp. This, combined with the one-piece design, contributes to a sleek and refined shoe that lends itself to black-tie events.

Shoes Every Man Should Own #8: Chelsea Boots

Easily recognizable by the elastic sides, the Chelsea boot is another staple of men's footwear and shoe every man should own by 30.

Initially, Queen Victoria had the Chelsea boot made for her because she struggled with regular boots. After all, the laces would often get caught in her stirrups while riding.

The original name for Chelsea boots was “paddock boots.”

Paddock boots became Chelsea boots in the 1950s as the style became extremely popular in the UK.

The Beatles and The Rolling Stones played a role in their popularity.

Both fanbases saw the band members wearing this style, and the Chelsea boot spread throughout the world.

The ease of these boots is what makes them a smart option for many men.

Chelsea boots hit at the ankle and have no laces. The sides have a strip of elastic, extending to the top of the ankle but not to the boot's sole. Typically, the elastic ends just above the welt of the sole.

Chelsea boots come in all different styles, making them easy to be one of the shoes every man should own. I recommend sticking with a leather style and avoiding suede for this boot.

Using leather for the upper will allow the boot to be more versatile and go well with jeans or a pair of trousers. However, that's not to say you shouldn't try out a stylish pair of suede Chelsea boots!

Shoes Every Man Should Own #9: Espadrilles

Espadrille came from “esparto,” a coarse grass in Spain and North Africa used to make ropes and high-quality paper. This grass also made the sole of the shoe initially.

Today, Espadrilles are still a popular menswear option and an excellent option for the year's warmer months.

Try to stay away from patterns and stick to straight colors with your pair. This will allow them to fit with more outfits.

Shoes Every Man Should Own #10: Boat Shoes

Paul Sperry (yes, that Sperry) created the boat shoe in the 1930s, and they are a fantastic option for men during the summer season.

With its moccasin-like style, a boat shoe can be a versatile summer shoe when worn correctly. This isn't a shoe to try and dress up in any way. I recommend wearing boat shoes with shorts.

You can get away with wearing them with pants but make sure your pants have a taper of some sort at the bottom. Wearing boat shoes with boot-cut pants would look very strange.

Also, this is another shoe I recommend wearing without socks or with no-show liner socks.

Once broken in, Boat shoes form to your feet and become extremely comfortable to wear.

There you have it, gents, 10 essential shoes every man should own. But do you know how to keep those shoes smelling clean and fresh? Check out my guide on how to stop shoe stench for good.

Click below to watch the video – 10 BASIC Items You Need To ALWAYS Look Stylish: