I remember back when Pokémon Emerald first came out. I was so excited that I pre-ordered it and got a little collector's tin. That game was so much fun! I had already played Ruby and Sapphire, so getting to play both versions in one was awesome. Brendan and May's updated outfits were a huge improvement over their Ruby/Sapphire versions and remain my favorite outfits to this day. Unfortunately, I sold that and the rest of my Pokémon games (Silver, Ruby, Fire Red, and Colosseum) several years ago.
Back then, I used to think that the white part of Brendan's hat was part of his hair. For this drawing, I purposely made it so that you could look at it either way: As a hat or as hair.
I couldn't really tell how May's hairstyle went, and I was too lazy to look up more reference pictures, so I just made it a bob around her entire head.
For the Pokémon, I drew Torchic on Brendan's side since that was the starter I always chose during my first playthroughs of R/S/E (Blaziken is awesome!). Naturally, May gets Mudkip since your rival always chooses the element your starter is weak against.
Brendan, May, Torchic, and Mudkip © Gamefreak, Nintendo