In OP's image, left is a cool as shit outfit perfect for him, but right I quite like too.
Anyway, Gary is the superior Blue/Green. While people whine and bitch that Ash is dramatically different from Red (I don't think they were very different before Red was mute), Gary is spot-on for a portrayal of the gen 1 rival. He is a cocky Eddie Haskel like piece of shit. He has a car & cheerleaders to crank it up to 11, he's being carried by that Oak money, in contrast to Ash who's poor from his dad abandoned him after knocking his young mother up.
Gary also has more going on than this, being an actual pokemon nerd/know it all which comes out sometimes like in the diglett episode. He and Leaf would come off better if they cranked up the nerd rival/nice rival aspect, like gen 5 has going on. It makes sense he is Oak's grandson. Gary also mellows out like Green later which is nice, though he becomes a professor instead of a gym leader. And he doesn't become ambiguously in a relationship with Ash as Green does with Red, which is a shame imo.
