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I wear a pair of brown Sketchers boots regularly. They're dressy-casual and look good with denim, khaki and cargo pants. They also make me taller! I've also gravitated away from T-shirts to long-sleeve casual stuff from Tommy Hilfiger and the like. You can get designer stuff cheap at Ross if you want to start testing out looks without spending a bunch of money. I also second the recommendation to browse the Maxim and Stuff fashion pages the next time you're near a bookstore.
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"The idea that money doesn't buy you happiness is a lie put about by the rich, to stop the poor from killing them." -- Michael Caine
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