backward hats? Is it still the 90s?
T-shirts are acceptable in the gym, the garden. Same for trainers. Joke T-shirts on adults are the saddest sight. Replica sports tops are never acceptable in any circumstances.
Most men look terrible as they get older because they get fat - when you get fat, your arms don't grow as your belly grows so shirts rumple in odd because the proportions are wrong. Then they couple that look with some shapeless jeans that look like they have just robbed them off a homeless person.