Iris was said to be able to communicate with Pokémon. This could be her given story in the show and I think the reason why she looks so different from the other females we've had is because she is different - going by this theory. No other female character could communicate with Pokémon or have any kind of special ability as such. So to go with the gift, she gets interesting clothing. Beyond that, I don't really care. She's kind of cute in my opinion and as of right now I'm more interested in her role and character in the show than how she looks. Whether I like her appearance or not, I'd still eventually grow to liking her.
I actually see her as the replacement to Brock. She's not game-based therefore she can travel with Ash for many more generations to come. Plus, she has a darker skin tone like Brock so the writers won't have to worry about fitting Brock back in the show like before when we had Tracey. I see the boy (if he is a traveling companion with Ash) as the replacement to Dawn. He seems very much like the kind to take part in Contests or Pokémon Musicals and by his look he can come with a very significant personality.
Speaking of the new boy, his clothes are cool in my opinion. I like his style quite much. His face on the other hand, I don't know, his forehead seems a little too big and his eyes too small - or I'm just being too picky. XD; Regardless, I'm hoping he travels with Ash and Iris. I can see him partaking in Contests (I pray that Pokémon Musicals are not a major part in the anime, I rather it be a one-time thing like when the Pokéathlon made an episode and that's it). He could come from a very wealthy family and have a very confident and high personality, thinking he's better than many, but really just starting and learning to realize that. I think he can make for quite the comedic relief as well. n_n;
It hasn't been confirmed that he is Ash's rival, and while it is still possible, we'll have to wait for further confirmation. I'd like him to travel with Ash and Iris though, but the personality I portrayed could fit well with him being the next Paul-like rival to Ash [i.e. Rich, Confident, Strong, and feeling as though he's stronger than most because he only seeks for the best].
Sue me, but I have high hopes for Best Wishes. It definitely strikes me as the writers want to change things a bit. To be honest, I'm all for it. It's about time we get things differently compared to the past thirteen years now. :(