When I feel like a bum i wear a cardigan over a t-shirt and jeans, and white Common Projects. If Im going somewhere that requires wallet and keys then I'll grab a field/moto/safari jacket. I think I have about five of them, and am always interested in more. Love the pockets. And they can run all across the casual spectrum.
I recently picked up a pair of PRL charcoal wool cargo pants that looked better than I expected. They go great with pretty much everything.