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What do you mean he dressed shitty? Every photo I’ve seen of him he has a collared shirt and slacks on which is what people in Medellin wear if they’re older than like 55. I live in Medellin and see lots of older guys dressed like Pablo.
He just wasn't very fashionable. He dressed like a nerdy dad dropping his kid off at soccer practice. That stands out as an oddity to me for one of the most powerful men in the world.
Example:
He's fashionable for here in Medellin is what I'm telling you. I live in the city and damn near every old guy I see dresses the same as him. You can find plenty of photos of him wearing suits but most photos show him wearing the fashion of the times, a light cotton patterned short sleeve collared shirt with slacks.
Here is a photo of him in a suit:
I guess I still think he looks frumpy there. Maybe it's more his overall appearance than his attire. How he wears the clothing, not just the clothing itself.
I’m pretty sure that at the time that photo was taken he was in the middle of running for political office and hiding the fact his money came from drug trafficking. I assume that look you described was exactly what he was going for.
That makes sense. I was actually wondering if his goal was to appear less intimidating, and more average. I think it could also lead to his enemies underestimating him.