What I wonder is the process through which we decide what looks good and what does not.
This is like second order harmonics of style, for want of a better phrase.
The paralanguage buffs tell us it's not what we say, but how we say it and what we look like when saying it, that's actually important in conveying a message. On SF WAYWN, it's about how we translate that message into the second order (photographs). Clearly, good photo quality, good selection, a narrative structure and other details in photos will affect perception.
Style is very much about a narrative; conveying a message. The more you can control the medium and the overall environment in which your message is received, the more an audience can be enculturally trained to be more accepting of the message. This is one of the principles behind good advertising (even so-called guerilla or viral advertising which seems on the surface to be freer) or good propaganda (much the same thing). One theory of dress would be that we are trying to "sell" a narrative message about ourselves to the world, however subconsciously.
Translating that from the real world, into the SF world of the WAWYN thread, it's clearly much easier to control the WAYWN environment than it is to control the real world, so if care is taken about this, it will have an impact on our interpretation of people's outfits.
This is delving close to the fertile territory between psychology and aesthetics, an interesting field for sure.