Just found this forum post on Ask Andy About Clothes, a cool website that "is devoted to men's clothes -- what to wear, how to properly wear it,and the history of why we wear what we do.
But, it appears that Andy is not a fan of square-toed shoes: "[Andy went into a store and] stopped in and spoke to Reggie, who wasn’t in such a great mood! I don’t blame him with all those ugly sweaters and square toed shoes to sell. Poor
guy." 
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January 24, 2007
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FWIW, historically I was not a fan either. I received a pair of square toed dress boots for my birthday a few years ago, and kind of like them now. Your mileage may vary,
taw
Posted by: Terry Weadock | January 17, 2008 at 01:40 PM