This was mostly cringey because of who he is.
But people don't realize that the clothes we associate with old people and maturity is really just the same clothes they wore as young people themselves. People don't switch to old people fashion when they grow old. Their fashion just gets associated with old people once their generation gets to that age.
This was thrown off a bit with us because hiphop has now spanned three generations with largely the same fashion sensibilities except is regards to sizing. So our fashion is still associated with hipness and young people despite being 40 years in the making. but in the past this was always the case.
A breh dressing like this in 1950s
versus an old head dressing the same way in 2020.
is literally the same thing.
but it's more accepted because we associate that style with maturity more than we do with sneakers, baseball caps, and bomber jackets.