Our Tips for Finding the Right Flip Flops for Men

By Steve George

November 19, 2019Fashion

Sandals are the first type of footwear man has ever made, but it is also the footwear that flip flops originated from based on findings on murals from Egyptian times dating back as far as 4,000 B.C. But the flip flop we have today mostly resembles the design of those worn by ancient Greeks – with the strap resting between the first and second toes.

Although this is the case origins-wise, the modern-day flip flop was actually popularized by Japanese culture with their rich history of Zori sandals, which became the most common summer footwear in the US during the 50s. While they were first mostly worn by women, soon the male population caught on the trend and by the 60s they were already a fashion trend. Fashion and trends aside, when it comes to choosing the right flip flops, you should mainly focus more on all of the important aspects that make a pair adequate for your feet.

mens comfortable flip flops


The base, or rather the sole of a flip flop should match the shape of your foot and provide proper support too. A good sole will also be thicker and have a low heel – this type of mens comfortable flip flops will provide you with great shock absorption. So before you make your purchase, make sure the base is as wide as your foot and that it gives you enough support to walk around comfortably.


While this is an obvious one, a lot of people wear their flops with their fingers and heels hanging a bit from the sole and not only does this not look good but it is also bad for your feet. Flip flops shouldn’t match the length of your foot either, you want to go for a pair that will give you a bit of room, usually slightly more than 1cm from the edge of your foot to the edge of the sole.

Moving Around

Although walking around in flip flops should be comfortable and strain-free, that doesn’t mean that they should jostle around like crazy. Trying to keep them on while walking around freely shouldn’t be part of the experience, but if they are moving a bit while walking that’s fine.


Trying on mens comfortable flip flops should be done at the end of the day because the feet are going to be a bit swollen which can helps you find the most comfortable pair.

Size Guide

Measuring the size of your feet is the most important part of finding mens comfortable flip flops that will thick all the boxes. What you’ll need is two pieces of paper, a ruler, pencil and some tape.

• Start off by taping both pieces of paper on a flat surface;
• Place your foot on the paper;
• Using the pencil, mark the heel and the longest toe (usually the big toe) with a straight line;
• Take the foot of the paper and measure the distance between the two lines;
• In case you notice that one foot is bigger than the other, use the measurement of the bigger one;
• If the measurements of your feet fall in between two flip flop sizes, go with the size nearest to your feet’s measurements.

Dangers from Flip Flops That Don’t Fit Properly


Mens comfortable flip flops shouldn’t be too large as if they are, they can affect the balls of your feet when walking which can lead to some areas becoming extremely painful and feel like you have a flame in your feet. This is a condition referred to as Metatarsalgia.


Wearing big flip flops that make your toes grip onto them constantly can make the muscles in the feet work for a long period of time which can lead to a condition called hammertoe that makes the affected toes bend at the joint in a hammer-like shape. This condition can render stretching the affected toes very painful and it can make walking long distances difficult. Usually, the second, third and fourth toe are the ones affected by this condition.

Ankle & Heel Pain

An inadequate pair of flip flops won’t be able to offer proper support which when worn for a long period of time. This can cause strain to the ligaments of the heel and the arch. This condition is usually the number one reason for arch and heel pain which in medical terms is called plantar fasciitis – it can get very bad over time, so much so that you’ll require treatment.

uncomfortable flip flops problems


Certain areas of a flip flop can rub against the skin and irritate it to the point where it can be painful to walk. This occurs mostly with, you guessed it, larger flip flops as sliding all the time creates the ideal conditions for the material to start rubbing against your skin. This creates calluses that usually look yellowish and are lumpy to the touch, but sometimes you will only get thick and hardened skin. If calluses become painful, you should seek medical help.


Blisters can be caused both by a tight flip flop and a larger one. When you wear tight flip flops usually the skin between the first and the second toe gets irritated and this causes it to form pockets of fluid in the affected areas. This delicate skin area can be affected even by the sheer sliding movement of the Y strap.

Back & Hip Pain

Poorly fitted flip flops can also cause pain in the hips, back and even the knees. This is usually the case if you have a pair that’s too tight or too loose as this way there is little to no support provided for the heel and arch. This can be the cause of an unsteady gait, bad alignment, straining in the knees and lower back.