i wish i could buy my boyfriend these

First of all I'm not a fan of 'freshness' as I call it, but I'm sure you know exactly what I mean. When boys wear clothes that are up to date and don't look like they have been lived in, I think it always looks better when not every piece of item looks so pristine and new, I like it when items look as though they have been worn and importantly they have a story to tell, i.e clothes who have a had a long shelf like for instance. Anyway as y'all know I want to be a costume designer, and after long debates with my head I have finally decided (for now) what and who my ideal character to dress would be. DUN DUN DUUUH. And it would be a young aspiring black musician who has I don't know say finally made his dream like most American positive Obama-generation films, who has had a hard life (kind of like a boy version of precious).
I know it would be obvious to dress the character in the 'freshest' clothes about and make sure he was wearing  over the top expensive clothes ( Kayne West style), and I suppose it would be more fitting to the character, as the character probably wouldn't have taste and like most 'rappers' they just buy the most expensive 'freshest' things that's on offer to showcase their money. Yet this isn't my ideal character to dress, I'd want a persona with more depth and some one who hadn't forgot their past and their struggle (1930's modern day gettho soul brother), so then them traits could  be reflected into costume...I'm thinking some sick ass fingerless gloves. Any suggestions?