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Tailoring Skillup Guide - 1-375
I found the best way to skill up tailoring is to create uncommon items with easy to get materials and then disenchant those items to get some money back (by selling the items you get from disenchanting).
The reason for this is that you'll usually make around 10 or 15 of each of the items, and to sell those at the auction house would take forever and some probably wouldn't sell at all. So ask your nice enchanter friend to bear with you on this, but it'll make it a lot cheaper to skill up tailoring. Also, it doesn't cost anything to put the items you get from disenchanting up at the auction house. So if they don't sell and you have to put them back up at the auction house, it won't cost you a thing.
One thing to note is that I've only included the skillups you get from making cloth into bolts when the recipe is orange to you. You can continue using those recipes for longer and get cheaper skillups from those, but as they are not guaranteed, I haven't included them. Probably the best thing to do is to look at the shopping list I've included at the end of this skillup guide. The shopping list will show you how many cloths you'll need in total (to make the bolts you'll need). So each time you reach a point where you can make cloth into bolts - check the shopping list and make the amount of bolts listed. This should maximise your skillups from making bolts and probably leave you with some extra bolts at the end that you can sell on (because you'll need to use fewer bolts for other recipe skillups).