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That's exactly why I do not let women dress me. They dress me up like some Cabbage Patch doll.
I think a great outfit for a man that straddles that fine line between dressy and casual is dark jeans (nice ones - no rips or tears or weird washes), a button up shirt (not necessarily super formal, but not slobby either - think stylish casual), and a sports jacket/blazer.
Location: somewhere close to Tampa, but closer to the beach
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Doubt i could..i am attracted to a woman who dresses like one..i have sat back and observed which women got more attention and it has always been the ones not dressed in sweat pants..sweat suits..eekkk..and long t-shirts..
And yes, since i do not really wear them much, id allow my Girlfriend to help pick me out a suit or two..just remember..skinny ties only..and nothing red, orange, yellow,..or pink..
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