He had unlimited resources, and was associated with people who were fashionable and members of high-society, but he himself almost always wore really ugly clothes. Was it a statement of his power, that he didn’t need to worry about his appearance, or did he just not give a shit?
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’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.