Packing with Lion, Part I

Alright! I am awful at packing so I am trying to get prepared well in advance. Here are some things that I am considering taking:

CLOTHES
Sarong: People keep saying that these are basically the best things any traveller has ever packed on any trip to anywhere. I don't really like sarongs but who am I to eschew the wisdom of the travel gods?
Shirts: Can I get away with only three of these? Two for day and one for "dress-ups"? Apparently singlets are considered slutty especially on pale blonde tourist girls so I am kind of angling for t-shirts.
Skinny-ish cotton black pants that are hopefully vaguely stylish: If I can find such a thing. I figure they will dry quickly and transition nicely from day to night.
Not skinny-ish pants that are not at all stylish, colour TBA: Hot daaaamn I hate the thought of wearing cargo pants but they seem like they are a pretty useful thing to have. At least I could wear them hiking and such and with thermals underneath.
A couple of scarves & bandannas: A cotton one for casual/outdoorsy times and for awful hair days. A nice one for INSTANT STYLE. A nice toasty one for when it is cold.
Swimsuit: I am kind of torn here. On one hand you are not really meant to wear revealing swimsuits but apparently in Brasil you get LAUGHED OUT OF TOWN just for wearing an American-style bikini! (Apparently the bottoms look like nappies.)
A light-ish jacket: For days that are not incredibly cold.
A warm jumper: I have a Mountain Designs one, and it is horrible and unstylish, but at least it is fleecy and toasty.
A warm jacket: That fits over the warm jumper. God it's not like I'm going to the Antarctic, maybe I'm just being silly.
A warm hat: For my cold head.
Gloves: Socks for the hands
Two (?) pairs of warm socks: For hiking on chilly days.
Three (?) pairs of sport socks: For chilling on Chile days.

FOOTWEAR
Black low-top sneakers:. For day wear. I have a pair and they are pretty alright, they are more comfortable than Converse low-tops but look better than regular sneakers.
Hiking boots: I don't have any. They are heavy to carry, a pain to wear in and kind of an investment. But a spot of hiking seems probable so maybe I should just go ahead and invest.
Some kind of shoe that I can wear to a restaurant or nightspot: But what? Maybe just black ballet flats.
Rubber thongs: For the beach, oh man seriously do I really need to take four pairs of shoes?

TOILETRIES

Toothbrush: Don't Forget Your.

Toothpaste: Also useful

Hairbrush and hair ties: For my hair.

Mascara and eyeliner: You got me, I am vain. Well-spotted.

Razors: Still vain. May decide to eschew these eventually, but I want them to begin with. To feel at home.

Sunscreen: Can you buy 30+ in South America?

Soap/shower gel: Which is better? I figure that soap is less likely to explode in my bag.

Shampoo/conditioner: Two-in-one makes my hair kind of greasy, but maybe it just needs to get used to it?

Medication with letter from doctor: So I don't bleed to death once a month.

Nail clippers: I figure I can use them for other stuff too.

One of those fancy towels: Are these expensive? Maybe I'll ask for one for Christmas.

OTHER
iPod: On one hand I think I wouldn't mind leaving this behind. But it would be good for keeping my Spanish podcasts and phrases. Opinions?

Lonely Planet: Look this is going to be my first ever international trip without a parent or guardian and I am basically just trying to survive.

Passport & photocopies: Note to self! Important!
Big old notebook: Containing addresses and emergency contacts and all that business. But also for writing things in. OH and a couple of photographs of family members etc., apparently the locals are into that kind of thing.
Pen: Okay this list is getting silly and I am really bored so I am going to stop making it for now.