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Apprentice Tailoring - 1-75
The word for this level is is 'linen.' Be prepared to use quite a bit of it in your leveling. When at all possible, avoid using patterns that call for bleach, dyes, or extraneous supplies like light leather. This will help you keep expenditures down.
Levels 1-50: You can hit the first landmark just by turning your linen cloth into bolts. Hang on to these, you'll need them for the next several levels.
Levels 51-75: Linen bags are your best bet here for speed and reliable leveling, but they won't sell to Enchanters. Alternatively, you could craft Brown Linen Robes or Heavy Linen Gloves; both take only Bolt of Linen Cloth x2 and Coarse Thread x1.
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Journeyman Tailoring - 76-150
Now it's time to move into wool for your nefarious crafting purposes.
Levels 116-125: Heavy Woolen Gloves is your best friend here, requiring only Bolt of Woolen Cloth x3 and Fine Thread x1.
Levels 126-150: Double-Stitched Woolen Shoulders stays 'yellow' up through the end of your Journeyman toils.
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Expert Tailoring - 151-225
You'll be using quite a bit of silk and mageweave for this stage of your Tailoring, but the good news is that you'll be crafting mostly 'green'-quality gear that disenchants and sells well on the Auction House.
Levels 150-185: Azure Silk Vest is good for quite a few levels, and even though Blue Dye x4 are included in the mats, at least these are available from a Tailoring Vendor and you won't be beholden to either friendly skinners or the Auction House market.
Levels 186-215: Green Silken Shoulders are great for this leveling period, requiring no extraneous materials outside of Silken Threads.
Levels 216-225: Black Mageweave Gloves will bring you to the end of your Expert stage and into Artisan. Be sure to also hit the Shadoweave Tailoring Trainer at this point, for some great recipes you won't find elsewhere. For the Horde, that's Josephine Lister in Undercity, and for the Alliance, seek out Jalane Ayrole in Stormwind.
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Artisan Tailoring - 226-300
Levels 246-250: Pick up the Tuxedo Pants pattern from the Tailoring Supplies vendor in either Ironforge or Undercity for this last leg - HAHA! - of your Expert journey. The mats are minimal and these pants often sell rather well for a novelty item.
Levels 251-255: You can nab a few levels here just by turning your runecloth into Bolt of Runecloth - and you'll be using a lot of it, so every level counts!
Levels 256-265: Grab the Tuxedo Jacket pattern to match those pants from earlier and gain 10 easy levels with minimal mats.
Levels 266-280: This is where Tailoring starts to get expensive. You have two choices here: either Runecloth Cloaks, if you happen to have access to Ironweb Spider Silk, or Frostweave Gloves if you'd rather shell out for the Blue Dye x2 for each set.
Levels 281-290: Runecloth Gloves are your cheapest option here.
Levels 291-300: Finish this stage with several pairs of Runecloth Pants. Congratulations! You've made it through the Vanilla-WoW stages!
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Master Tailoring - 301-375
Levels 311-315: Netherweave Belts and Netherweave Bracers. Both recipes take minimal mats, and both items disenchant into the Arcane Dusts needed in order to make the specialty cloths.
Levels 316-330: Netherweave Bags still sell remarkably well, and the mats are not exorbitant.
Levels 331-340: Netherweave Pants are definitely your best bet at this level, and again, they disenchant for mats needed later.
Levels 341-355: Netherweave Robes - are you seeing a trend here?
Level 350: It's time to make your choice in specializations. Will you choose Primal Mooncloth, Shadowcloth, or Spellcloth? While it doesn't matter so much at this stage, your choice will impact your end-game Tailoring specialization as well. Priests will prefer Primal Mooncloth or Shadowcloth while Mages and Warlocks will choose between Shadowcloth and Spellcloth, depending upon preferred talent spec.
Level 351-370: Bolt of Frostweave. That's right, you'll be crafting in Northrend for the last stretch of your Tailoring leveling.
Level 371-375: Frostwoven Belt puts some of those Bolts of Frostweave to good use, and finishes out this stage of your career.
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Grand-Master Tailoring - 376-450
Yes, you've done it! The pinnacle of your Tailoring profession, and you're in the home stretch, now. Once again, skip the Outland level 70 epics, and don't look back.
Level 396-405: The Duskweave set of Belt, Cowl, and Leggings gains you 10 levels here.
Level 406-415: Duskweave Wristwraps, available at 400, will bring you up to 415 easily.
Level 415-420: Remember that specialization you took back at level 350? Now you will be able to craft the blue-quality Northrend special cloths. Once every 4 days, make your allotment of Ebonweave, Moonshroud, and Spellweave. Hang on to whichever type you'll be using for your personal set, and trade the others for more of the same.
Level 420-435: The Black Duskweave Robe is an awesome piece of crafted gear, and you should be able to sell these about as quickly as you can make them. As an added bonus, crafting these robes will bring you within 15 points of maxing your Tailoring.
Level 436-445: Gain ten levels by crafting the hand-warmers of your choice, either Ebonweave Gloves, Moonshroud Gloves, or Spellweave Gloves. All of those specialty cloths are coming in handy now, and you want to make sure you're crafting those as soon as your cooldowns are up.
Level 446-450: The final stretch is always a pain, but you can count on guaranteed levels with the Glacial Bag pattern. This 22-slot bag will sell for quite a bit, and you may be better off advertising the crafting when your customer provides his or her own mats.
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You have reached the end of your leveling and you are now a max-leveled Grand-Master Tailor. Too bad they haven't made a title for that, huh? But at least you know that you are able to use any of the epic patterns that may drop in your guild's raids, and you can help your friends and guildies out with cloth gear, shirts, bags, and novelty-wear for the best-looking bank alts around!