I believe that you'll find that most of us here hike in trail runners instead of boots. I resisted the switch for years, but when I changed I found that trail runners with anti-pronation support in the footbed provide far more support. I couldn't turn an ankle even when I deliberately tried to do it! It is the footbed that supports your ankles, not that piece of leather around the ankle.
As for socks, cotton is pretty much a no-no when hiking. It soaks up moisture and takes forever to dry (what's the last thing out of the clothes dryer?). On your feet the constantly wet (from sweat) cotton socks cause blisters, and on the rest of you wet cotton can lead to hypothermia. I've used both all-synthetic and merino wool-synthetic blend socks and far prefer the latter, although both are good at wicking moisture away from your skin. The wool feels dryer even if it isn't, and I have no problems with it in hot weather. Interestingly, in the past I couldn't wear wool at all--all hail those merino sheep!
If you haven't already found them, there are lots of excellent articles on gear and clothing selection listed in the left-hand column of
http://www.backpacking.net/, the home page of this site.
Another good site for gear selection is
Mark Verber's website. Lots of ideas for gear, including low-budget alternatives.