Well, historically clothes were "tailor made" for whoever was going to wear them. That did not mean clothes weren't inherited, only that they were made to sort of fit the original wearer (the loose terms are used because the clothes were usually made within the household, not by a professional tailor). Obviously, nobility is a different case, as were expensive armor.
I'm not sure Toady is "shying away" from the issue: rather, it's not obvious how to implement it in such a way that it both provides player control (for those who want it) and ease of use. Guilds would be a potential point to rectify the issue whereby you could turn things around to have dorfs request production of items and then pick them up later, but you'd have to find a model whereby you're able to flow that down to cloth production->farming/husbandry in a manner that's possible to understand and control at the desired level of detail, including handling of shortages (you don't want some dorfs to go naked with the clothing having rotted off their bodies because other dorfs consistently manage to order new production at the slightest sign of wear (or just a desire to hoard stuff) when you don't have enough to keep everyone equipped.
Another issue is that a lot of clothing production means a lot of worn clothing disposal...
So far I haven't encountered anyone that won't wear race appropriate items.