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Personally, I've become addicted to Hollister. The pants are comfortable, and the button-up shirts look nice enough for any casual situation. I will admit that I could definitely use more formal clothes, but I rarely have occasions that require suit and tie. I tend to stay in natural colors and well away from black.
When I do get snazzed up though I have about ten or so dress shirts and (a lot of) ties that tend to once again stay in the natural tones to go with my three suits.
As far as shoes go, running/tennis/basketball shoes were intended for those activities. I've got some old ankle high 'boots' that I wear with every day pants/jeans when it's cool outside, 'boat shoes' or flip-flops for shorts or in the summer, and square toes for going out on the town.
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"Two roads diverged in a wood, and I-
I took the one less traveled by,
And that has made all the difference." - Robert Frost
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