I'd like to get a pair of motocross style boots for trail riding. The benefits seem too obvious. For general riding, I've been wearing above the ankle hikers or my Georgia work boots. I like the ankle coverage when I'm riding.
As for protective wear and armor. I bought an Alpha branded jacket from Amazon. It is made from an abrasion resistant cordura and has removable CE pads at the elbows, shoulders, and spine. It has a removable liner that is very warm and the jacket is supposed to be water proof, but I haven't tested that. I expect it will help mitigate road rash and protect my joints a little. It has reflective print, bright white, and safety yellow, so maybe I'll be more easily seen. All that for $60. No, it's not a seatbelt, airbag, or get out of injury free card.