No longer relegated to a banker’s office, the wingtip (AKA brogue) has rapidly become a very cool shoe to own, for both work and play. But to pull this look off you have to purchase the updated version of the classic shoe (look for elongated tips and thin soles) and know what to wear with them.
What makes wingtips great is the juxtaposition of style. The rest of your outfit (or the majority at least) should have a modern look and fit to it, with the traditional roots of the shoes injecting a dash of character into the entire outfit.
I have a great pair from J&M (they no longer sell them), that I wear with everything. They’re made out of antiquey, burnished leather, so there’s a very masculine old school feel. When coupled with a modern outfit, it’s a great statement because it’s so unexpected.
I typically like going with a brown, slightly distressed shoe, because it’s not as buttoned-up as a pair of black ‘tips. And distressed black is more difficult to pull off without looking slobby.