The point is that these people don't care about fashion or watches or how much you spend on your clothes. They dress conventionally instead, which is a standard that only changes over the scale of a decade or so. The mistake outsiders make is to think that the point is to follow fashion and buy an expensive watch. That's why they don't fit in - they wear something fashionable.
Also, to defend the idea a bit, the idea of a dress code is exactly that purpose - so that you don't need to worry about what you're wearing or how much it cost or wether someone thinks it's fashionable or not.
The point is that these people don't care about fashion or watches or how much you spend on your clothes. They dress conventionally instead, which is a standard that only changes over the scale of a decade or so. The mistake outsiders make is to think that the point is to follow fashion and buy an expensive watch. That's why they don't fit in - they wear something fashionable.
Also, to defend the idea a bit, the idea of a dress code is exactly that purpose - so that you don't need to worry about what you're wearing or how much it cost or wether someone thinks it's fashionable or not.