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Make studded Gorglet till you hit 100%, then next item on list, up until until(switch when you hit 100% success) then switch to leather do to finish off...
Factions my friend. It is by far the easiest way to get to legendary tailor. Join a faction/get killed by opposing faction/temp skill loss=easy way of raising tailoring. Skill loss lasts 20min I believe.
Its a worthwhile practice for all sorts of hard to raise skills. Lockpicking/taming/poisoning/tailoring. These are all skills I know people use the faction skill loss to train.
u can raise till 119 tailoring making studdeds, beyond that, only bone armor will raise your skill, try to use the GGS to prevent countless hours of hard work to gain 0.1
get one ur char in one faction and your 100 tailor to other one... kill the tailor.. he will loose -33 skill.. and go make oil cloth.. skills will come back norman about in 10-20 minutes so u can gain skills to 120 VERY fast and cheap.. thats all i guess