This would be my idea for the Pokémon squad in real life (this is based on looks and my opinion, it could be that you have a completely different idea of them)

Chloe G Morgan as May Maple

Francisco Lachowski as Drew Hayden

OR Colin O'Donoghue (BECAUSE HE'S AMAZING!) as Drew Hayden 

(He could also work with Gary)

Edward Cullen as Gary Oak (Not a Twilight fan, but Harry Potter :P)

Kristen Stewart as Leaf Green

Anna Popplewell as Dawn Berlitz

Brant Daugherty as Paul Shinji

Alyson Hannigan as Misty Waterflower

Skylar Astin as Ash Ketchum

And that's it for now! Maybe I'll update it later with some more, if I got time!