I think it could be seen from a few different directions. Everyone has different impressions of what jobs "mean" and what personalities are attracted to them - some more different than others. And this can diverge even more if people try to make the outfit fit their understanding of not only the world, but their character. I would imagine there's more overlap for "this definitely doesn't fit" than "this is what fits." and then the fun vanishes as people try to impose "correct lore" on one another, lol.
When I slap a glamour on Moose, I try to pick something that takes his past and experiences into account, too. Maybe he wore that Nymian AF for a couple weeks, but he was engaging a new experience and trying for authenticity (or whatever). "Getting his head in the game."
And since 2013 / 2014 I've been slightly modifying the same outfit he fell into - a Nymian mortarboard for easy identification (because he's short), a Lominsan bliaud because it's modern, functional, and had long been associated with the Knights of the Barracuda (
Lominsa's military, not Nym's), whatever pants and boots best fit the bliaud but look like I could walk in them anywhere without worry for his feet, and fingerless gloves so he can still put finger to page and write with dexterity. All in jet black because ... uh ... I'm not even gonna front:
h*ck yeah black, purple, and silver trim.
I put a lot of effort into it "fitting scholar" but also fitting the personality I think attracts scholars, and Moose himself. But I expect someone out there thinks that's bogus.