If you buy lots of clothes and don't play with some protagonist for a while you will find that the AI will dress the protagonist individually.
And in a ridiculous way.
One time I see Franklin wearing his baggy yellow shirt with longsleeve underneath all ghettoish, but his trousers were some plaid dress pants in grey and some fine shoes.
Michael wore colours which wouldn't fit and a dress jacket but shorts below.
Trevor, well, f*ck it. He is a binco explosion victim.