I'd personally NOT get a messenger bag ... even though I use one all the time.
But I get compliments on mine sometimes, its made by Roots. They're in your price range anyway.
BB fitzgerald is a pretty young cut, especially if you slim it in a bit. Last I checked they had clearance fitzgerald cotton suits for $200. Been considering getting one.
Ordered 6 recently. Got them in about 2 weeks.
The only drawback is that there is no visible logo to let everyone know what fine socks I have. I remedied this by removing the turkish stamps on the package, and then pinning them to my...
Keep in mind that goodyear welted shoes are resoleable, so assuming you care for them properly, they'll live longer then the 50 pound shoes. Does it fully offset the price? Maybe not, but over time, the price difference between low end...