If we go by the standard of "being asked for directions by a native of the place when you are actually a tourist," it seems I look right at home in Vancouver, Victoria, Montreal, Manhattan, Brooklyn, Boston, Seattle, London, Manchester, Nice, Antwerp, Dusseldorf, Berne, Zurich, and even (once) Milan. I'm sure I'd also get asked in Glasgow, Edinburgh, Oslo, Copenhagen, Stockholm, Amsterdam and a host of other places that I haven't been (yet).
It has nothing to do with a chameleon fashion sense. I just look non-threatening and also, usually, neat and presentable.
I think I look most "at home" in Toronto, which makes sense -- it's where I was born and where I lived in young adulthood and it's the place where I most intimately know the unspoken rules and codes. I know when I'll want heeled booties and when I'll want the Blundstones; I know when jeans will be right and when I'll want something dressier. I blend in, even when I wear a red coat while most others are wearing black.
But I feel best in any urban centre where I've brought some of my favourite and most current, fashionable clothing -- preferably one where the environmental norm is a bit dressier than my current city's, and where the climate is more temperate.