I've spent my life going places and getting into places others can't and I've lived and traveled in everything from high crime areas that make a 3rd World Country look good to 3rd World Countries.  

Back in the draft days, it was the Army taught me, even if its not your style,  cut your hair, where a neat uniform, and shine your shoes, you can get away with murder.  It's life that has taught me the same principle applies except you extend it to whatever dress/style it takes to get accomplished what you want to.  When I did business in TX, I often had three outfits in my car and could go from three piece suit to cowboy boots and jeans.  

There's no pat answer to this one.  Sometimes you want to blend and others you want to stand out saying mess with me I have enough money and influence to screw your life up.  Others its mess with me, I'll shoot back which is a fine line to shoot me first.  These are all decisions that have to be made around the scenario and within that time frame.

Like all things in survival, its a matter of learning to adapt.  There's times you want to be Grey and there's times you want to stand out.  

Now that I've stated the obvious, the trick to pulling it off is being comfortable projecting what image you want to project.  One of my favorite very graphic examples is put a guy in a tie that never wears one, you can tell right off the bat he's only worn one to get married if then.  The same goes dressing down.  You can put a bums gear on but nobodies going to buy you are a bum.  Like all things survival, it depends on preparation.  You need to be doing this before its a matter of life or death.  

I'll give you an example, my first trip to Poland, I took the Polish Airline.  The entire long flight the stewardesses all talked to me in English.  On the way back, they spoke in Polish to me till they learned otherwise.  It wasn't jut what clothes I put on but the mannerisms and not just what I said but how I said it.  Simple things like inflection, hand gestures, and body language.  If you are not tuned in on these things, you are going to stand out like the urban cowboy wearing camo at a Gun Show.  

Now I'm not saying go put on your bum outfit and go downtown to hangout or put on your Rambo outfit and go visit the closest Army fort.  What I'm saying here is you need to start paying attention to such things.  You don't have to become them.  Its little things, the highlights, and impressions will be made.  

I could write a book on inflections and gestures that set first impressions.  You can too.  All you have to do is pay attention to those automatic impressions we ourselves get.  In my Poland example it was simply saying "Yes" not once but three times like you understan, slightly nodding, while using your hand like waving off a fly, "Tak, Tak, Tak.".  I learned to fit in in China where an Anglo stands out like a lone mountain in a desert.  You see its not just dressing the part, in fact, I'd dare say that's very little of it.  Its actually fitting in.  Acting like you own it.

No kidding, acting like "I own it" has gotten me into places you wouldn't believe possible and out of jams that you would think getting out impossible.  

Tj