Less so now, but in the early half of the decade Businessweek was known for its unorthodox, and often lighthearted style of graphic design. This still survives on in the Businessweek 404 (When will Businessweek get its sh!t together?!), but the corresponding 404 for Bloomberg itself has been replaced by something more sober.

I think I tend to trust outlets more if they don't pay so much attention into keeping up with the design style of the day.

Overfocus on this shallow surface quality has a correlation with a lack of underlying quality in the actual content. It's not that you can't have both or that I don't appreciate surface quality. But if something is ugly or simple or doesn't follow trends and has great content, it tends to remove a certain sort of person as consumer and perhaps lowers the temptation to cater to shallow desires because not many are around to get hooked.

That is, many things are better because certain parts of them are objectively worse and turn away certain people.

Looks like a "Brutalist" design, which is becoming more popular. A sort of reaction against standardized design patterns (Material, iOS). some examples here: http://brutalistwebsites.com/

I think that's completely purposeful...gives off a "Pepe Silvia" conspiracy theorist vibe https://knowyourmeme.com/memes/pepe-silvia