My travel's all pretty much for vacation, so obviously my needs can vary. I wear my everyday boots (a nice pair of Irish Setter branded boots by Red Wing), and I find that for my purposes they can go with pretty much everything I wear up to a suit (at least if they've been cleaned recently). I wouldn't wear them with a tux (which I've pretty much vowed never to wear again ), but I do wear them for formal nights on cruise ships. From there, I'll also typically pack a pair of sandals because they're significantly smaller and lighter to pack.

Of course, that also basically represents my entire collection of shoes.