So I'm working on my first cosplay ever and was gonna dye my hair but didn't think i could get it long enough in time for anime north. That aside I'm trying to cosplay as Gildarts Clive from Fairy Tail
It will depend on you head size. But for the length in the back I would go with the Matilda. Trimming is not horrible to to for a deginer you just t=have to take it slow. Also some people bring the wig to the hair dresser and wear it while they do the trimming. (with a refernce photo).