Wellington is like a small part of San Francisco in USA, but with taste of wild ocean weather.
soippa: If you want to look like local, wear "flipflop" shoes or walk without shoes. Other hand, women look feminine with skirts and in high heals when visiting city centre. Looks like that for most of working places you need to dress up little and people wants to follow fashion, in Kuba street you see more hippie style. When it is raining again, local disappear and you can spot tourists wearing raincoat or shell suit all day long. Local walk on the left side of footpath. Tourist guide told, that they know all homeless people by name, so this is quite a welfare city and caring society.