I dont see whats wrong with him wearing the clothes that were in style when he was younger. Dudes on here make fun of people his age wearing skinny jeans and shyt, cant have it both ways.
Seinfeld used to have a standup bit about his dad where he said you can always tell what was the best year of a man's life because his clothes stay frozen in that style for the rest of his life.
It only seems strange to us now because the first "Hip Hop generation" is getting older. In the next couple decades look for baggy jeans and fitted hats to replace high-waisted trousers and white belts as the stereotypical old man clothes. Gonna be weird
The thing with Jay or Nas or whoever.. when is time to suit up, they do it big..they do it right. I have no problem with them wearing what they wear. Slim jeans are fine IMO.
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