You can start tailoring fairly early once you have the kit if your character has no problems with beating on wolves. With ruined wolf pelts and patterns you can begin your career making small sized patchwork armour. However, there is a reasonable failure rate doing this and when you fail both the pattern and the pelt are lost. A more efficient way of starting is to wait until you can beat up on real spiders and collect spider (not spiderling) silk. Combining 2 spider silks makes 1 silk swatch and never seems to fail. Doing this you can work your skill up to level 15 without losing anything, then go back to patchwork if you want to progress to 26. This way you'll have less lost pelts and patterns.
Alternatively for the wolf and bear loving types, from 15 you can start making raw silk garments to sell to casters which will take you to a skill level of 36. If you're making garments simply for practice and not planning on selling to players, stick to making the items that only need one silk swatch - no point wasting 2 swatches on pants or robe unless you actually need pants or robe!
At this point you have another choice on which way to go, but either route starts to get expensive. You can move on to studded leather which requires metal studs from a blacksmith. Either you make good friends with a blacksmith, pay about 1pp to a smith to buy them, or take a break to go practice smithing and make some. Whichever method you choose, studded should take you up to a skill level of 68.
The alternative method is to go to the brew barrel and make up a batch of heady kiola to make cured silk garments for monks. The ingredients for heady kiolas are quite expensive and depending on your brewing skill failure rates can be quite high. If you opt for this route cured silk will take you up to a skill level of 82. Again, if you're just doing this to increase skill and aren't trying to sell the proceeds for profit, stick to making lots of masks as these use up less components on each attempt.
Personally I did a bit of both, but making studs got tedious so I gave up and concentrated solely on cured silk. The good news is that quivers are finally working and rumour has it that making quivers (the normal ones, not fleeting quivers) can take your skill up to at least 115 before becoming trivial. As these only require a pattern (expensive pattern at over 1pp though :( ) and a high quality cat pelt, this looks like a far easier option than making reinforced leather to raise your skill above 82. The downside to quivers is that they are a container, so make sure that you have at least one main inventory slot free before starting to sew - and it's helpful to be sitting beside a merchant so that you can sell your successes as you go. If you feel masochistic enough to want to try the reinforced route this will take your skill up to 108.
Tailor made backpacks are the same weight as normal backpacks but have 10 slots instead of the usual 8. These are the reason most people take up tailoring! Making the packs becomes trivial at around 88 skill but as the high quality bear pelts that you need for them are very hard to find (and can cost anything from 25pp to 50pp to buy from other players!) I'd recommend not even thinking about them until you've got your skill as high as it can go to cut down on your failure rate. Once you reach the happy stage of being able to make these reliably you can finally start to make some money back by selling them to other players for something in the 100pp region.
And the latest news is that spiderling silks can now be used in tailoring! Two spiderling silks combined make a silk thread and 2 silk threads make a silk bandage. Unconfirmed rumours suggest that threads go trivial around skill 22 and the bandages around 26. However, before you run off to whack those spiderlings - a couple of points to note. Unlike silk swatches silk threads seem to fail quite often so you can lose a lot of silks while trying to improve. In addition, people who have done the maths estimate that the money you would earn by selling the four silks needed for each bandage is more than the cost of buying a normal bandage. And by buying, you'd be guaranteed a bandage for every four silks you sold - no such guarantee with tailoring them. So, although this looks like a gift from the heavens for the melee types that use a lot of bandages, the economics suggest that it's only really of use for improving tailoring skill until your skill level is such that you rarely fail on the sewing.
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