Note, if this is just not possible I understand.
Both in order to both create some thought to what you wear in cities and to kind of suggest the player is advancing up the ranks, why not have expensive clothes that give bonuses? Specifically the bonuses I was envisioning would be to the kind of skills use use in the cities, like Charm, Roguery, Smithing, Trade, or maybe even Stewardship. This could also help with companions who you assign to work properties. Of course make such clothing maybe be less useful if you do still get into street fights. I would also of course suggest so as to reflect that these items are not worn by all to have these items both be rare and cost somewhere in the low to mid four digit area.
Both in order to both create some thought to what you wear in cities and to kind of suggest the player is advancing up the ranks, why not have expensive clothes that give bonuses? Specifically the bonuses I was envisioning would be to the kind of skills use use in the cities, like Charm, Roguery, Smithing, Trade, or maybe even Stewardship. This could also help with companions who you assign to work properties. Of course make such clothing maybe be less useful if you do still get into street fights. I would also of course suggest so as to reflect that these items are not worn by all to have these items both be rare and cost somewhere in the low to mid four digit area.