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I actually hate it when I match too much! Grey, brown, blue-throw it all in! I love his yellow socks, denim shirt, and the spotted scarf. What I love, is that he seems to be dressing for himself. Not for attention (it's not like he's wearing a stop sign!) or praise. I think that's how your look should be...for yourself, not for others. Take some risks, take some chances, but don't put on a costume every day.
The world of fashion is a balancing act...wearing the trends while keeping true to yourself and staying simple. Don't sweat the small stuff.