Newsflash: you’re getting older and older and you don’t even know what shoes every man should own by the age of 30!

Granted, you have until you’re 30 but let’s get a head start on it now.

When a person judges your status, they look at your shoes.

Gents, it’s time to upgrade your shoe game.

In this article, I am going to go through 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.

It’s time to flex your footwear muscles for everyone to see – let’s get started.


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Click here to watch the video – 10 Shoes Every Man Must Own (2020) 

Shoes Every Man Should Own by 30 – Contents

  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


1. Cap-Toe Balmoral Oxfords

shoes every man should own oxfords

The 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 is how you can distinguish an Oxford shoe from a Derby shoe. A good quality Oxford shoe is made with a box-calf leather and should not have any broguing.

From job interviews, weddings and black-tie events, an Oxford is an extremely versatile dress shoe 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 is characterized by the extra piece of leather added across the toe box.


2. Tennis Shoes/Sneakers

shoes every man should own black sneakers

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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 were first made 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 shoe maker 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.

shoes every man should own white sneakers

Featuring a clean white Italian Napa leather, these sneakers from Thursday Boots will certainly stand out.

By the 1950’s, tennis shoes became a staple in almost all children and young adults wardrobe. 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 are worn too much. I recommend owning a classic pair of low-top sneakers with a leather or suede upper.


3. Wing-Tip Brogues Shoes

shoes every man should own brogues

At the turn of the 20th century, Irish workers wore Brogues for outdoor work.

Interestingly, the patterns or Broguing we see on Brogues today that make them so distinct actually had a practical purpose.

The holes were actually punched all the way through the shoes. The shoes drained water easily that would catch in them without taking them off which saved time and money while the workers were on the job.

Elegant versions of Brogues began to worn by many including male and female actors and entertainers after being used as country and outdoor shoes until the 1920s.

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 to usher in a new era of the shoe.

types of brogues infographic

There are many different types of brogues but we would recommend going with a “Full Brogue” or “Wingtip” as shown above.

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 easily with dirt and dust.

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


4. Chukka Boots

shoes every man should own suede chukka boots

Yes, boots are part of the shoes every man should own by 30!

With a strong sport and military history, chukka boots have become very popular and are a must own boot for any man.

Originally 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 true 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 which is 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 just to name a few.

I recommend a suede chukka boot in a dark color such as brown or navy.

You can get a normal 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 they are made out of a coagulated latex that is very flexible but not durable.


5. Double-Monk Strap Shoes

shoes every man should own double monk strap

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

This was later adopted by an Englishman traveling and taken back to England. However, this has not been confirmed or proven.

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

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

shoes every man should own double monk strap

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 really flex a lot of your creativity with these as you can get different type of buckles with many different buckle placements as well.

Click here to check out my ultimate guide to Double-Monk Strap Dress Shoes!


6. Penny Loafers

shoes every man should own penny loafers

With Norwegian roots, the first Loafer was produced in 1936.

Fisherman in Northern Europe in the 1930s had been seen wearing 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 normal 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 and it creates a small pocket or slot in the shoe.

Penny Loafers are typically seen as more relaxed than other dress shoes.

Loafers will help to add a bit of flair to your summer suit style as you will typically wear lighter colored suits such as cream or blue in the summer months and not a black or charcoal suit.


7. Whole-Cut Oxfords

shoes that every man should own black 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 designed to be understated and elegant.

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

In addition to this, the leather must be a 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 shoe laces are attached under the vamp. This, combined with the one-piece design, contributes to a sleek and refined shoe which lends itself to black tie events.


8. Chelsea Boots

shoes every man should own chelsea boots

Easily recognizable by being able to slip them on and off with use of the elastic sides, the Chelsea boot is another staple of men’s footwear and shoe every man should own by 30.

Originally, Queen Victoria had the Chelsea boot made for her because she struggled with normal boots because 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.

Fans of both saw the band members wearing this style and the Chelsea boot spread throughout the world.

beatles boots

The Beatles suited and Chelsea booted for the night’s performance!

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

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

Chelsea boots come in all different style. I recommend sticking with a leather style and avoiding suede for this boot.

By using leather for the upper, this will allow the boot to be more versatile and can go well with jeans or a pair of trousers.


9. Espadrilles

shoes every man should own espadrilles

The name espadrille is derived from the word “esparto” which was the name of a coarse grass in Spain and North Africa which was used to make ropes and high-quality paper. This grass was also used to make the sole of the shoe originally.

Espadrilles hit their peak popularity in the 1970’s and especially the 1980’s when Don Johnson wore espadrilles throughout the entirety of the television shoe Miami Vice.

shoes every man own

Espadrilles offer a lot of ways to flex your expression with different colors and designs.

Today, Espadrilles are still a popular menswear option and a great option for the warmer months of the year.

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


10. Boat Shoes

shoes every man should own boat shoes

Paul Sperry (yes that Sperry) created the boat shoe in the 1930’s and they are an amazing option for men during the summer season.

With their 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.

mens boat shoe

Perfect to wear near the water, Boat Shoes are back and better than ever.

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

Some will say that boat shoes are “trashy” and not a good option for men to wear. I would say if worn in a casual manner and correctly, they aren’t trashy at all.

As stated before, men have a very limited amount of summer footwear that isn’t a flip-flop or sandal. Don’t be afraid to experiment!


Shoes Every Man Should Own by 30 – Summary

Now, get out there and start shopping before you turn 30!

If you own these 10 shoes, you will have better footwear than 90% of other men.

On top of that women will certainly notice.

Now that you are attracting women with your choice in shoes, click here to check out my guide on how to attract women easily or check out some of our other articles below!



The post 10 Shoes Every Man MUST Own by Age 30 | Essential Men’s Footwear appeared first on Real Men Real Style.

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By: Antonio
Title: 10 Shoes Every Man MUST Own by Age 30 | Essential Men’s Footwear
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Published Date: Sat, 26 Sep 2020 11:55:02 +0000

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