How do you know what amount and type of gear to bring on a trip? How do you know that you're prepared without being too excessive? I see some people wearing shorts and sandals on miles long hikes, while others are carrying the equivalent of a UHaul on their backs. If you've ever brought too much or too little (or not the right stuff) share your tale.

Going to hike a few trails in ONP at the beginning of June, only hiked a few times on small, well-kept trails in the Cascades and somewhere in NC with some friends. No idea what to wear, pack, or bring. Joggers and tennis shoes? "Hiking" pants, boots, and some expensive jacket?