Fitting In: The REAL Gray Man

The Gray Man, an almost tired subject addressed countless times on various prepper blogs / youtube / whatever.  I think I’ve even written about it a few times but lately I’ve been thinking about it so buckle up, here we go again.  Before we get into attire let me ask you a question:  You walk into a bar or small local restaurant, you are greeted as a local with head nods -OR- you are given the cold shoulder and looked upon suspiciously by the crowd.  Which do you choose?  Another example: You are on vacation (pick a place) and you are relentlessly American, to an obnoxious extent (read: you ask for the club sandwich and fries at a restaurant in Eastern Europe while wearing a Grunt Style T Shirt with 40 lbs of extra gut hanging over the waistline).   Is that really how you want to come across?  If the answer is “Yes I am who I am no matter where I am” this post is not for you.

Attire Based on Location

I have a good friend who has a friend who, checks out google maps and other information sources on locations to see what people are wearing (styles) before going there so he can adjust his wardrobe in order to blend in.  Generally speaking jeans and a T shirt will cover most wherever you are but I have several outfits that I use.

– Classic hiker guy: La Sportiva boots, Kuhl pants, Patagonia et al.
– Chill bro guy:  Sweat top and bottom, Adidas shoes, backwards hat
– Suburban guy:  Express jeans, button up collared shirt with sleeves rolled twice, Cole haan leisure shoes
– Backwoods bro:  Carhartt’s, Mossy Oak, you know the drill
– Sophisticated bro:  Tailored suit, no tie, white shirt
– Milspec guy:  All the gear, maybe even a Shemag

I could go on and on but these are just examples of clothing styles I utilize based on the location / city I’m in, group I plan on interacting with.  People are infinitely more comfortable interacting with someone they relate to, someone they believe is one of them (see the local bar example listed above).  As such they will communicate more openly and freely, be more polite, generally just make things easier to navigate for you.

The Concept of Blending In

Act like you’ve been there before, that’s the entire point of this.  I have walked into locations and stated something like: “this is who I am, I need access to your back room / warehouse / files / restricted areas” and they almost always are like sure, it’s all yours.  You can dress how you want but the confidence to blend in, to be part of it, to act like you’ve been there is paramount in achieving success as a gray man.  Someone who can move in and out of scenarios and leave little if any trace, while achieving desired objectives.  Now we aren’t talking industrial espionage here but maybe there are other less non-criminal applications that you can come up with which suit your own personal objectives.

People Aren’t Stupid

As a gray man, you have to be prepared for 2nd and 3rd layer interactions when trying to blend in.  Think about the bar scenario for example, you really don’t want to give people your personal information but you do want to interact, be prepared for those next level questions or have the ability to steer / re-direct so as to keep things smooth but avoid the personal stuff.  If you simply answer everything with “I don’t want to talk about it” or “that’s top super duper secret” you’ll arouse suspicion, but if you can artfully direct a conversation and keep things surface level while seeking connection points things will go well.  Connection points are things that allow you to turn the conversation back to them, people love to talk about themselves.  Maybe during the course of it all you find out their kids play soccer, quite the opportunity: “Oh really, my sister played soccer in high school, what’s the level of competition like these days?”  Sit back, 30 solid minutes where you don’t have to talk.

The Bottom Line

This isn’t Spy vs Spy.  Blending in and looking for dead drops isn’t what we are after here and blowing our cover isn’t a life threatening event.  Yet through it all I’m sure you are like me in that you don’t want the attention in almost any setting.  You’d rather sit back, observe, inject when you need to and then float off into the ether entirely unrememberable when it’s all said and done.  Thoughts on gray man?  Leave them below.

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