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Thread's kinda dead but oh well, here's mine. Regular temp clothes on lefts, simple and classy looking, and colder temp on the right, with a nice sweater in between. Any number of the small things like the lighter, food, pens, pokeballs, etc. Soap, shampoo and cologne for feeling fresh as fuck every day I wake up. Also a large number of that, as well as the clothes, come to think of it.
The food, lunchmates because they're fucking delicious. Also, Groudon pajamas to look menacing as fuck while I sleep. A journal to keep track of my journey and a comfy as shit sleeping bag. Also, an iphone, and a 3ds for entertainment purposes. As for the Pokemon; Mamoswine, because it's a beast, and it can carry me, or my backpack full of goodies when I'm tired. Mareep because fuckyeah sheep, and it can charge my electronics for me, Quagsire because he's a bro, and he can provide water for washing myself and my clothes. Tropius also for carrying purposes, flying, and a fresh supply of bananas every once in a while. Camerupt for the fire, and carrying purposes. I'm a lazy fucker. And Linoone because he's my truest bro. He'd be my starter, as I'd be from Hoenn and fuck takign the normal starters. Also that pickup ability would come in handy.