Having a mutli-tool in your coat pocket is great, but I think the coat is more important. (boringer, but more useful.) But the biggest prep?
Pay attention. To the weather, your surroundings, abilities, news, etc. and so on.

Before you go out hiking for the weekend to Mt. Baldy, check the forecast...

In the military we called it Situational Awareness -- S.A. for short.

I have an 18 year old son, who's a really great kid, but for most of his life, I couldn't seem to get him to look at the weather before going into work. He worked as a courtesy bagger at the local store, running groceries in and out for customers.

Winter seemed to drag on through spring this year, with several warm days followed up by a sudden cold snap and sometimes a sudden wet snow that would leave a couple of inches of slush on the ground.

One morning, they were predicting such an event to hit that particular evening about an hour after my son started his job, and around the time I would be getting home from work.. He sat with me thoughout the morning newscast, saw everything that I saw. He watched me put on my boots, and grab my coat going out the door.

It just didn't register, and today, I decided I'd let him figure it out for himself.

Needless to say, on my way home from work, with the wet snow pouring down, my son calls me on the cell phone asking me if I can bring down his coat and boots, that he was already soaked.

Needless to say, traffic slowed my progress home, and it took about a 1/2 hour for me to get to him. I asked him why he left without proper clothing. I asked him if he noticed me putting on my Duty boots that morning, and grabbing my coat... and if he had even been listening to the weather that morning.

He said "Yes Dad...".. Then I asked him why he wasn't prepared.

Honestly, it pretty much came down to him being a somewhat lazy typical 18 year old... but after experiencing NOT having the right clothing for the situation, I noticed he started carrying some kind of jacket or coat around in his trunk no matter what the weather.

Sometimes you have to let them experience the problem a little for them to really learn.

RNewcomb-best way to teach them, is by letting them figure it out, then ask for help. You've toggled that switch!