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?
He wanted to be popular with the regular, poor people. He was throwing money left and right but always denied where his wealth came from. He wanted to come across as a self-made, honest man. Some believed it, or just weren't willing to accept the atrocities he was capable of. He was overthrowing the government, blaming it for everything that was bad in Colombia, and wanted to appear as a savior, hence the contrast he was creating by wearing simple outfits in certain public appearances. But he did also wear suits and shirts that were considered tasteful and fashionable at the time.
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.
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.
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.
Why bother with such a useless thing as stylish clothing when you have everything you want already? Wearing something you feel comfortable in makes much more sense in this scenario than wearing something you look good in.
I guess that depends a lot on the person. I feel most comfortable when I look good in what I'm wearing. Even if it's just a T-shirt and jeans, it needs to fit right and compliment my appearance. Most of his clothes look disheveled, and ill-fitting, so I guess he just didn't care.
Of course it depends. I don't really care how I look, because no matter what I wear I'm still no Brad Pitt. Quite the opposite tbh. So I strongly prefer casual and comfortable clothes whenever possible. And I don't really care if one part fits the other. The only exception is I don't wear red trousers when I already have red t-shirt... lol