You can automate the tattered clothing thing!
In your assignment tab, go to the outfit menu and for each outfit change the condition to 51-100%. This will tell your colonists to not wear anything less than 51% condition clothing.
In your tailor bench, set up some jobs to keep a minimum stock of X items for each bill and change the condition in that as well to 51-100.

Now your colonists will strip any "tattered" clothing (condition 1-50%) and automatically put on the available clothes that aren't tattered. As they take the clothes, your crafter/tailor will eventually spin up a new item to replace the one that was taken.