Work boots are tricky to get ahead. Some lines slow 6", while others say 8" boots. CPR requires puncture resistant soles. Most major companies subsidize, or even pay for them outright, depending on the agreements. They also usually have lists of the brands and models which are acceptable.
Look into bags, like Autumn Creek, and Tuff Bag. They are designed to hold up to the rough use. A plain Walmart brand won't last very long. First find out what books you will need to carry, so you get one which is big enough. I had a railroad Tuff Bag, but now it isn't practical. As a conductor, it would fit my rain suit, lantern, books, and so on. Now I don't need those items, so I have a bag which is a computer bag/brief case with wheels. This keeps my books better organized.
Breathable rain gear is a wise investment. Go to an industrial supplier. A set that a hiker wears will not hold up to climbing over boxcars.
The whole exercise is to be prepared like a good Boy Scout, but not be overly incumbered if you need to walk down the tracks, away from the nearest road. The conductor which I just worked with is just the opposite. He carries way too much, and has to make multiple trips.
A leatherman tool is often handy. I also have a separate set of toiletries. This way I don't need to unpacked, and repack before, and after each run. The only thing I do is take out dirty laundry, and replace with clean clothes.
Clothing is one other important point. Of course dress for the weather. Pack at least 2 changes. This serves two purposes. First, you may get wet or dirty. Second, the return train may get delayed. This may lead to a whole hotel day. After that, you will still need a set for the return day. This lesson was learned the hard way. I once had to wash some clothes in the hotel room sink, and dry them on the radiator. I got called for a "local", which turned out to go out, lay over, and mark themselves for the return, on their rest.
I hope this helps.
