I don't want to go all AAAC on you (because I'm hardly trad), but that is a pretty trendy style right now. Johnston and Murphy has an ad in GQ with Lyle Lovett wearing a similar shoe.
Here's a link to the pic:http://www.johnstonmurphy.com/catalog_chooser.aspx
I think, for $40, it wouldn't be a horrible purchase. But, if I did purchase it, I would likely wear it the four or five times in a year that you mentioned, then donate it to charity. Definitely not a style that will remain "in" for long and not one I'd wear with a suit; I'd consider it with some odd pants sans jacket and tie but would more likely pair it with jeans, chinos, or cords.
The shoes I'm proposing aren't necessarily exciting, but they might somewhat inexpensively meet your desire for a lighter colored shoe you could dress up a bit.http://www.ctshirts.co.uk/product.as...ProCode=MSHNBBhttp://www.ctshirts.co.uk/product.as...ProCode=MPSBRBhttp://www.ctshirts.co.uk/product.as...ProCode=MPSCND
The first would be $125 with the current 50% Tyrwhitt promotion code. The second two would be $150. Not exactly in the $40 neighborhood, but certainly not in the $500+ range for the brands mentioned frequently on this board. At the 50% discounted price, I think the Tyrwhitt shoes are a good value. I bought a pair of the first ones last year (the second, calf version, wasn't offered at that time, or I would have bought them) and have been reasonably pleased with them. I believe it has been determined that Loake makes Tyrwhitt's shoes, though I'm not certain.
On edit: After typing my response, I re-read your first post that you were looking for something in a more Italian style. So, these options probably don't meet your needs. The third option is a bit more sleek than the first two options, though.