Most of the first sets for Warlocks followed the original WW1 design ideology with trenchcoats. The Watcher drops in Trials have that style, although a little less shader friendly.
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Yeah, and sadly I am not the great when it comes to the trials. I think part of it is I just want to have fun when I play PvP and the trials just ruins it for me. Wouldn't mind getting those robes though since I do plan on using a black shader.
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The Watcher gear drops for losing teams, too. You could run in their with a Khostov and a broken trigger and still get it.
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Yes, but you also need a team (unless they added matchmaking to it) and as far as I know that aren't really any teams that would play just so somebody can get a legendary chest piece to drop (especially when I am want intel stats). But I may give it a try and see.
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Good Luck.