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Divide your gear into systems for easier organisation.
Take into consideration what you'll be doing, in what terrain and what climate/weather you anticipate.
A few examples.
>Clothes
Jacket, pants, underwear, socks, boots, hat, gloves, insulation layer.
>Cooking
Stove, pots and canisters. Cutlery, cup. Something to carry water in.
>Shelter
Tent/tarp, sleeping bag, sleeping pad, pillow.
>Tools etc.
Knife, axe, saw, GPS/compass, map, fire starting kit. First aid kit, hygiene kit (toilet paper, soap, toothbrush).
Things good to have: Cordage, duct tape and plastic bags.
If you use boots it's nice to slip on some light weight running shoes or sandals.
If you're going invest in something your priorities should be good boots/shoes and backpack.