The Ultimate Shoe Regret

Men, do you have a pair of shoes you regret purchasing? Most of us have at least one. At the time of purchase, the shoes looked sleek, sophisticated, and adaptable. But, let’s be really only took them out to one fancy business dinner or event. They haven’t seen the light of day since. 

Buried in the dark shadows of your closet, you give these shoes a quick glance thinking, “oh yeah, I should wear those again.” But the truth won’t. Or at least, you wont wear them anytime soon.

We’ve heard all the excuses again and again: 

“They looked cool when I bought them.”

“I thought I would have more formal events to attend.”

 “The sale was too good to miss.” 

and the list goes on and on. 

The fact is we don’t judge you. Buying a nice pair of men’s dress shoes is no easy feat. And if you haven’t noticed, the business casual world is starting to change. 

We no longer have to dress as our grandparents did in the office...full suit and shiny black oxfords. Companies like Goldman Sachs and Virgin Atlantic are becoming more flexible in how they define business casual leaving more options for us. 

But now we are back at square one. With so many different shoes to choose from, how do we find the perfect pair of casual dress shoes? Presenting… the high-end sneaker. Some would call it “the best dress shoes for men,” but we’ll let you come to that conclusion on your own. This sneaker takes you from day to night as a flawless companion to your high-stakes business meetings and a classic addition to your night at the bar. 

By following our minimalist guide below, you are sure to pick casual dress shoes that fit your style and of course your foot. Guided by the three main principles of versatility, comfortability, and durability, this guide provides a comprehensive checklist in finding your next pair of shoes. 

The Minimalist Algorithm for Finding the Best Dress Shoes for Men


Versatility is important for a shoe to become a top favorite. The best shoes are the ones we can wear to multiple events and with various attire. Keep your current wardrobe in mind to accurately answer these three questions. 

Do the shoe colors match most of your daily work attire?  

When in doubt, go neutral. When choosing a shoe, shades of black, white, or brown are safe colors. That means you will be able to wear them with most of your wardrobe. However, the safest bet is to choose the brown sneaker.  Brown sneakers pair well with many shades of jeans, khakis, or slacks for optimal versatility. 

Is the design simple enough to wear to work as well as other social events? 

We live in a fast-paced world that demands spontaneous reactions. We may get off of work at 5 and have concert tickets for 6. The time for spending hours in front of a mirror to prepare for an event is over. We need casual dress shoes that turn from day to night without the hassle. 

Do they stand the test of time?

Yes, we all want to be in fashion. However, in pursuit of a minimalist style, you should check to make sure that your casual dress shoes are not just a yearly fashion. In fact, the first dress shoe was created in the 1600s and started to catch on in the 1800s in England. That is the kind of longevity we are looking for in a shoe. 


No matter how cool the shoe looks, comfort is key. While we might be willing to sacrifice comfort for a few hours, a great men’s dress shoes will be one that we look forward to wearing. 

Am I wearing the right size of shoe? 

Finding comfortable men’s dress shoes means choosing the right size for your foot. A shoe that is too large or too small can cause blisters and redness. Each shoe manufacturer has a different size guide. For KOIO, they recommend sizing down if you wear a half size. If your KOIO shoe doesn’t fit right on delivery, return them for a different size with our free shipping and returns policy. 

Are they made of comfortable material? 

Your schedule is busy and you have long days. Finding casual dress shoes that provide cushion and comfort throughout your day is of highest importance. Reading the materials is a key indicator of comfort. Out of the many choices of material, leather is sturdy yet supple material that provides comfort in style. (Check this out if you’re looking for some of the most comfortable leather you will find.)

Is it okay if they are uncomfortable at first? 

The short answer is yes. As long as you have the right size, certain shoes will take a few wears to break in. The best advice is to wear them on shorter days to let the shoe contour to your foot. After the third or fourth wear, you should be experiencing the nice fit of comfortable casual dress shoes.  


Investing into a highly durable shoe means less decisions. Finding the right men’s dress shoes for you means finding a pair you only have to replace occasionally. 

How long will they last? 

A good pair of men’s dress shoes will last you from 1 to 5 years. Depending on how often you use them, some will last longer than others.

Are they easy to clean? 

Sneakers are no good if they look dirty right away. A good pair of casual dress shoes will be easy to clean and maintain. Materials such as fabric and textiles tend to trap dirt in easier. Find a shoe made from leather for easier maintenance. 

Our Recommendations

If the shoes you had in mind didn’t pass the test, that’s okay. Thankfully we have some great recommendations. Try any of our men’s sneakers today at Each shoe is already pre approved to pass our minimalist algorithm.