Apparently I can't dress myself

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Another Note: I absolutely refuse to step in a [censored] Gap or its aborted cousin The Old Navy again. I appreciate those suggestions. I should have included this in my OP

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check out Express for some super metro button down dress shirts, just get either black or white to keep it straight. You can find two shirts for about $80

match the shirt with a pair of distressed-jeans, something not that expensive like Aber & Fitch jeans, run you about $65 each. Buy two, one darker shades, one lighter shades. DO NOT BUY ANYTHING ELSE AT THAT STORE, ONLY JEANS.

Drop by banana republic, check out their sale section, they always have nice longsleeve collar shirts or dress shirts from early in the season. Spend about $200 on stretch t-shirts, long a short sleeve, and try to pick up another dress shirt.

Finally, head over to Macy's or your local dept store, pick up a nice black pair of shoes to wear with your jeans. ~$100 for a decent pair.

your set to go

$80
$65
$200
$100

=$445 plus taxes

$500 and a semi respectable wardrobe to begin with

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Nice work, thanks