Boots vs Shoes - If you're doing any trail running or less strenuous hiking, you'll probably prefer low top hiking shoes. But, if you're taking longer hikes, on unstable terrain, or finding yourself around a snake or two, go for a true boot.
Material - I'm doing as much as one man can to push buyers back towards natural materials. Namely, I'll always advocate for leather boots. Vegan friends, I get your trepidation, carry on. Everyone else should wear a leather boot, in my opinion. They are just the best value, last the longest, and look the best in any scenario. That said, new-age polyester and nylon ripstops and composites are fine for most people, and they cost less than leather up front.
Outsole - You want the sole of your hiking footwear to be beefy and grippy. That way, you never lose footing on nasty trails, slick surfaces, or dusty rocks.
Waterproofing - Whether it's a GORE-TEX membrane or regular Durable Water Repellent (DWR) treatments, you're going to want some sort of something to keep water away from your feet.
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