I must say I love Jiraiya's outfit. I like the traditional touches like the geta. For that same reason, I kinda like Orochimaru's clothing too.
Tsunade's outfit is OK, but I dislike the 3/4 pants. That goes in general, though. I also disliker her shoes...
Young Tsunade, with blue cloak instead of the green, was pretty, though! Oh, Young Jiraiya was cool too!
There are, however, sooooo many outfits where I'm thinking "why dafuq would anyone choose THAT for fighting?! It's ridiculous - you'll trip or get caught! *Sigh*" I'm thinking Neji's sleeves, Utakata, omg, what utterly stupid outfit! Ino's belly-showing top. Ugh...
Also, I really, like, REALLY, don't understand an outfit like Kurenai's. Does she wrap herself up in those bandages every friggin day?