I think you need a chunky wingtip in order to make it work with denim. I.e. an alden longwing in #8 shell cordovan. I have black Balmoral Alden wingtips that are my business shoes and because of the slimmer profile, they look silly with straight cut jeans. Maybe with a really tapered leg you could get buy with a slimmer wingtip..
8/13/10 at 8:48pm