Ash looks great in anything but if I had to choose it would be his original outfit. :)
His AG outfit was my favorite, with is original one as second. Third is DP, and 4th is BW.
My favorites are Ash's BW outfit and AG outfit.
HAHA Nice to see so many Ash fans love Ash cross dressing like myself here :p
I thought he looked really pretty in the BW series, how can any guy not hit on him? They really need to do for one of these cross dressing episodes.
5. Best Wishes(BLack and White)
4. Diamond and Pearl
1. X and Y, I like how he has Red's hat!
My favorite is the XY outfit, followed closely by the OS outfit. I've always believed that, since Ash is the anime counterpart of Red, he should have an outfit that bears a resembles to Red's, especially the hat. AG, DP, and BW outfits didn't gave Ash Red's hat, which was always a disappointment for me. Luckily, XY finally did it and he looks awesome. The original outfit is a classic as well, a great tribute to the original design of Red, and it speaks of a nostalgia time when Pokémon were big, fun adventures that every child enjoyed; no competitions or no meta-gaming alike, just a fun time with your friends and Pokémon.