What do think Ash's clothes will be in Gen 5?

[Cuddy]

He probally have a different color hat, different color backpack, and a more modern style pokedex, but his appearance will probably not be changing all that much

 

[Moonlight Umbreon]

Black in everything,with black gloves.(any team rocket member would say:
''And the big R on the T-shirt!'')

 

[jinglejoe]

Maybe Ash could where Red's FireRed and LeafGreen outfit.

 

[peno]

But Red's FRLG outfit is just recoloration of Ash's AG outfit ;-)

P.S. Your comment wasn't really creepy at all until you added the smiley.

Gee, I knew I did something wrong. Wrong smiley :blush::sweat:

 

[Cybersai]

It'll probably be similar to the 5th gen males outfit

 

[Our Wasted Years]

A cheap Photoshop edit of his previous clothes.