@blue peterI like the contrast, especially with the thick-toed birks, but baggy pants would work as well.
Debating the purchase of a long shirt, I like the idea but just not sure if I'd get enough wear of it.
It's funny, I never really thought of chelseas as SWD specific. Maybe that's naive based on the ubiquity of CP/SLP versions in this thread. But like I've said before, I'm not a chiseled guy so I don't think a super chiseled shoe would really work for me.