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Person A= Is wearing a polo shirt neatly and tightly tucked in a pair of shorts. Wearing a belt with just a cell phone hanging on it. Also wearing some white socks and gym shoes.
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This is how I usually dress if I am out and about in a casual manner. The exception would be topsiders instead of gym shoes.
Your expectations would prove to be very wrong about whether I was armed. You could expect a .38spl J frame, or a .45ACP 1911 concealed on my person, depending on whether I left home in a hurry or not. If you messed up and let me get to my vehicle, you would find a 12 gauge in my hands.
A hoodlum might not think I was armed, I get your point there, but I'm not going to dress any different because it might make people think twice.
The obvious pick is the person unaware of his surroundings, regardless of his clothing. Criminals don't select victims based on who may be armed and who may be unarmed. They select victims based on how quickly they believe they can overpower them. If you are aware, it does not matter if you are wearing a Speedo and flip flops. The garden variety criminal will let you pass by and wait for the unaware or distracted victim.