So getting away from trainers or the usual black/brown plain chelsea boot or chukka aesthetic or even other less typical choices like Sperry's and brogued chelseas, I was thinking about what people thought about some other types of footwear. I'm mostly posting this because I'd like to get a bit more mileage out of shoes that I'd normally wear only for business. As I have about 15-20 pairs of EG/Lobb/C&J/Grenson/CT/etc... that I don't wear that much, it seems like they might work with some streetwear outfits. So for a fairly conservative choice, I think these would work fairly well, but aren't particularly interesting. Would something like the C&Js or Grensons be considered trying too hard with a mostly casual outfit? (polo/jeans or the like, no dress shirt) How about monkstraps? Or ankle boots? Lastly, is this look trying too hard? I have a pair of Gucci loafers that I almost never wear, and I have a hard time finding a situation in which I would wear them that wasn't casual.