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I completely get your, I wished I could get back to days where I hadn't thought about what I'm wearing. That's why I try to keep it simple with the one leather jacket. But now I'm thinking about the second one... stupid kid.
All my friends who have known me back then are disappointed in me now. They say, man it was so cool how you didn't give a damn about clothes. Or appearance in general. Apparently, a lot of people would comment on how shit I'd dress and I'd just lol at the fact that the rags people wrap themselves into play any factor in their lives...
And now I'm one of them.