Editor’s Note: I recently received the following email from a reader regarding my On the Grid column in Issue 29, When Going Gray is a Red Flag. In that column, I responded with an open letter to an acquaintance who had ridiculed the “gray man” concept — you can read my counterpoint on page 104 of that issue. This reader, who wishes to stay anonymous, offered some helpful insights into his experience with this principle as a plainclothes law enforcement officer.

The Gray Man silhouette


My apologies for being so far away from the release date of Issue 29, but I wanted to pass along my thoughts on going gray.

First, my background. I am a military veteran who did serve overseas (Cold War), and have over 18 years in federal law enforcement with over 13 of those years in plain clothes.

To me, it is a balancing act. A person should have clothing that is practical, good quality, long wearing, and comfortable. It should also match and reflect a persons style and taste, as we all have preferences that make us unique and comfortable. Your clothing should be appropriate for the area, but versatile enough for movement to other areas. A tuxedo and a business suit are similar in having a coat, shirt, tie, and pants, but they are not necessarily interchangeable. And no matter how good Cary Grant looked in “North by Northwest,” you wouldn’t really go mountaineering in that apparel.

Cary Grant looking dapper in the classic 1959 Hitchcock thriller

Cary Grant as Roger Thornhill in the classic 1959 Hitchcock thriller “North by Northwest”

I agree with, and enjoyed, your article. Just as a military veteran can often spot another, so can a true veteran spot a charlatan. The way a person moves/looks/carries themselves says volumes about who they are. And even those who have made careers out of deep cover assignments, understand the limits to going totally dark and yet still be engaged and relevant.

Another point to consider is this: in addressing crime deterrence, it’s recommended that the more hardened a target is, the greater deterrence it is to a criminal. If your home has alarm company signs posted, visible cameras (even fake ones), well trimmed landscaping, and visible quality locks, a thief would possibly pass it by in favor of a less prepared looking residence. The same can be said about a person. But a caveat is that there will always be an outlier that is not fazed one way or the other.

I would stress more emphasis on situational awareness and environment awareness, than stressing a “gray man” concept. One also needs to be within their comfort zone. Some people want/need a fairly comprehensive EDC to feel comfortable, while others are more minimalist.

Anyway, that is some of my two cents to a nickel’s worth of thoughts. If you wish to use any of my comments, feel free.

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