Practicality vs Style vs Comfort – A Guide for Picking a Shoe

Shoes are more important than most men realize unfortunately, and there’s more to choosing the right shoe for each occasion than just the brand or type. In fact, if you want to be one of the few impeccably dressed men around, you need to be able to categorize shoes based on their practicality, comfort and style quotient.

They need not always be found in the same pair, but that’s okay, as long as you are able to prioritize the right attribute for the right occasion. Stay with us as we attempt to go over the basics of selecting your shoes based on their practicality, style and comfort.

sutro charlton boot sole
The Sutro Charton boot


The practicality of a pair is likely the simplest to define, because unlike the others, it really does have a more universally applicable definition. A practical shoe would be any pair that fits the occasion. It goes above and beyond style, but does not exclude it either. For example, if you wore a sturdy pair of winter boots to a cocktail party, that would be highly impractical because that’s an absurd and unnecessary choice for the occasion!

On the other hand, you cannot wear your favorite piece of designer sneakers while you go hiking during the winter either. High-quality, durable sneakers would be ideal for a hike if it was in the summer, but winter is a whole different ball game, and that’s when those sturdy winter boots add practicality to your choice of shoe. The scenarios are numerous, but the idea behind them is more or less the same; in order for your shoes to be considered practical, the pair must match the occasion and the situation with perfection.

  • For formal occasions, try a pair of Oxfords; Allen Edmonds’ 5th Avenue is a standard go-to.
  • For casual occasions, you can’t go wrong with a good pair of boots. Thursday’s Captain is our pick for the most versatile, but for more casual offerings you might prefer a heavier pair of Red Wing boots
  • For semi-formal occasions, say you’re in khakis and a blazer, slim boots like Thursday or Carmina’s Chelsea are a good bet, or you can grab a pair of loafers — Grant Stone makes our favorites
Taft Jack boots 2
The Taft Jack boot has a Blake stitch, offering more flexibility than a Goodyear welt


Comfort is not as easy to define, although it’s still an easier concept to decipher than fashion or style. What would be comfortable for one person might be uncomfortable for the other, depending on the shape/size of their feet, their own sense of style and personality. A more direct aspect of comfort is related to practicality as well. For example, you cannot be wearing a pair of elegant loafers when it’s snowing or raining outside, even if you do look dashing in them. Your feet will be physically uncomfortable after they begin getting wet and cold.

Comfort is not just a physical aspect either when it comes to clothing. If someone is not mentally comfortable with wearing a pair of shoes for some reason or the other, they should not wear them. It doesn’t matter if the shoe is extremely expensive, has a comfortable fitting and is quite trendy, because we cannot be confident in a pair of shoes if they do not make us feel comfortable in public. Without confidence, it’s impossible to carry anything off in style.

  • Construction: Blake stitches and cemented construction are more flexible, and some prefer them to the resole-ability of Goodyear welts for that reason.
  • Outsole: If softness is your priority, you can get something with a crepe rubber soles, like a Red Wing moc toe or a Clarks Desert Boot. A dressier option for guys who like softer outsoles but want something sturdier than crepe is the leather sole, which you can find on the Carmina Chelsea or Wolverine 1000 Mile
  • Midsole/insole: Many prefer leather for both as they conform well to the foot over time. The standard for quality boots is typically a cork midsole and a leather insole, though some newer companies like Thursday and Oliver Cabell put in shock absorbing foam, like EVA
  • Arch support: If a boot has a shank, you can be fairly confident it has decent arch support. That said companies, like Parkhurst, allow you to purchase extra arch support. If you have serious issues with your arches and need inserts, be sure to purchase a less sleek, more voluminous boot like a Red Wing.

[Learn More: What are crepe soles? And, the best boots with crepe soles!]

nothing new modeling
In the snappy Nothing New sneakers


This is the most difficult aspect to define, since style highly varies from person to person, and even the big designers get it wrong sometimes. However, there is a close connection between comfort and style. Shoes that people find themselves to be the most comfortable in are also generally the most stylish shoes for them. This assumption is largely based on the fact that the more comfortable (physically and mentally) someone is in a pair of shoes, the more confident they are while wearing them. Given that confidence is the single most important factor in fashion, that creates a natural correlation between them. Add a dash of practicality or suitability to the choice in respect to the occasion, and you really can’t go wrong.For example, choose shoes that are always in style, like Chelsea boots, Oxfords or plain white sneakers. With these classic styles, you can’t go wrong! 

koio capri triple white side view
The very crisp Koio Capri

Practicality, Comfort and Style Need Not be Mutually Exclusive

Now that we have separated and discussed each of the aspects properly, it should also be understood that they need not be mutually exclusive. If, for example, we take high end sneakers like Koio, it’s easy to see how they combine practicality, comfort and of course, style.

On the other hand, a pair of boots with Vibram lug soles like Tricker’s or Truman are  hardy, practical and stylish boot that’s designed to offer practical protection to your feet as well as grip on slippery ground. (For more grippy boots, check out our guide to the best winter boots.)

As should be obvious by now, the three categories are often intricately connected, or at least when we do manage to get things right. More than anything, it’s our own ability to match the right shoe with the right occasion and the right attire that decides the practicality, comfort and style of the pair.

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I am a young, passionate writer with extensive experience in business, blogging, technology and personal development. Through my own experience I understand the personal growth journey from business novice through to a mature leader, and I infuse this knowledge into my content to offer inspirational articles that professionals from across the corporate landscape will enjoy and value.This blog shows my portfolio of some of the work I've done over the years so you can find out more. Contact me to see where else I have been featured.

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