A Mile In His Shoes

Posted by Kevin Estela on Feb 16th 2023

We’ve all heard it. “Don’t judge a man unless you’ve walked a mile in his shoes.” This idea reminds us to use empathy and seek understanding before we cast judgment. I’d like to say I am above judging others but realistically, I am not. We don’t live in a judgment-free society and each day, I make hundreds, maybe thousands of judgments. Judgment costs you nothing other than time and energy but it is extremely valuable. Being a good judge of character is therefore considered a compliment. The people we encounter daily need to be judged but what is a good way to systematically accomplish this? Depending on your background or mission, you may need to judge others more harshly than others. A simple judgment we all need to make for security is determining if others are friends or if they are foes. Other judgment helps us determine a profile of who we encounter. Much like a good detective, you can use powers of deduction to walk a mile in someone’s shoes and get an idea of who you are dealing with.


When I used to teach trail-safety seminars, one of the red flags that should alert you to someone having ill intent was mismatched clothing for the environment. Appalachian Trail assaults and robberies happen along the 2000 mile trek and some commonalities exist such as proximity to shelters where hikers relax and let their guard down for the night and encountering people on the trail who don’t look like they should be there. If you notice a person mismatched for their environment, they may only be there for a short time. Sneakers don’t belong where boots do. Looking at a person’s feet doesn’t have to look like judgment as many people lower their eyes as a sign of respect. From a distance, you may notice their clothing first but always determine if their footwear matches where they are. If not, a red flag should be raised until they give your reason to lower it.

Brand New

Used gear has character. I have a hard time believing someone has put in the time gaining experience anywhere if their gear doesn’t have a mark on it. We all know the serial gear collector who has multiple of a single item and never really gets any time behind it. Good for them for having the means to be a collector but shame on them if they never spend the time to learn one item really well. Ever hear the expression, “beware the man with one gun, he probably knows how to use it?” People who dedicate time on one weapons platform will have an intimate knowledge of it. Their gear usually shows plenty of wear. Think of how this applies to boots or shoes. Perhaps they are wearing boots they just purchased or were issued or perhaps they never use them, period. Brand new gear could mean you’re dealing with a “new guy”.

Well-Worn But Maintained

Brand new boots are one thing, well-worn boots are another. Worn boots can be indicative of someone who doesn’t maintain their gear and if they are willing to let something slide, what else will they let slide. Someone who has well-worn, broken in gear that is maintained says something about their level of responsibility and pride. We all know someone who applies maintenance to their vehicles, their firearms, their health (with regular checkups), or even just their bed when they wake up. I like a person who takes pride in their equipment. They understand the importance of it and don’t take it for granted. They also likely have plenty of experience that is represented by the character marks on their kit. Judging and stereotyping can be done with a very broad brush and there is a chance we lump someone into a category that they don’t belong to. However, this category is one that I’m usually right about and the characteristics of the person wearing those boots are usually accurate.


Ever look at a person and wonder how much they paid for something? That question applies to footwear and can give you some insight into their financial means. Footwear is available at many price points and there are some that are great values and some that are extravagant. Some boots are cheaply made and despite having the means to purchase better, the decision is made to skimp on the critical connection between their feet and the ground. Some people spend a significant amount on their footwear when they don’t have to. We can look at the value of a pair of boots and guess if they were purchased because of want or need. Is the person practical, are they seeking approval, are they seeking comfort and performance? What drives them? The value of what is worn on someone’s feet gives us some potential understanding to many questions.

Style and Purpose

There are some shoes that have a very distinct style and purpose. They are worn for one activity and there’s no mistaking why they are worn. Equestrian boots are one example and water shoes are another. Some shoes are closely linked to certain groups of individuals like Salomon low-cut “adventure racing” shoes with SF communities. There’s also a difference between running shoes and runner’s shoes. Anyone can go to a shoe store and buy running shoes but there are some brands of runner’s shoes that runner’s can identify. In a similar way, there are very specific hiking boots, hunting boots, boots for forestry, mountain hunting, wet-wading shoes for fishing, backpacking with crampons, and on and on and on. Your shoes or the shoes of the person you’re profiling/characterizing tell a story. When we run the 48 hour survival challenge where students live out of the contents of a Ziplock bag, it isn’t uncommon to see students double up their laces or swap out standard laces for paracord to use as emergency cordage.

Curve Balls

We’re not supposed to judge a person until we walk a mile in their shoes but what if they are borrowing those shoes? What if those shoes were “hand me downs”? What if they are wearing shoes that they were told to wear on someone’s suggestion. What if they grabbed whatever shoes they could find in an emergency? There are many reasons when a pair of shoes doesn’t line up with the person wearing them. I won’t say judging a person by their shoes is a perfect science, it is more like a soft science. There will always be outliers and times when you get it wrong. At the very least, learning to judge people by their shoes and making it a regular practice improves your situational awareness that should keep you safer than trying to live in an imaginary judgment free world.