Socks are probably the most overlooked item there is, and everyone cheaps out on them because good socks are expensive. Look for a cushion sole sock of 80% wool and 20 % poly for durability and comfort, and expect to pay around $20.00 a pair. The weight of the sock should reflect on your boot fit, and the weather.
Lots of people like ankle height boots, but I'm not one of them. I like the support and protection afforded by high leather uppers. Stitched soles are evidence of a superior boot, but glued on soles have come along way. I like the Acadia and FT. Lewis boots by Danner, although because I have a wide foot, it takes a while to break them in. Until the weather turns very cold, I prefer a minimal amount of insulation in my boots, because once a boot with heavy insulation gets wet, your feet are wet for the rest of the day. Around here it is seldom you can hike for more than a few hours without going over the tops of your boots in water at least once, and more often it happens throughout the day.
The country you hike in and the weight of the loads you pack should determine the stiffness of the boot. If you check out Mtn Equipment Co-op's catalog they have good suggestions on how to choose boots that are well matched for the country you hike and for the type of hiking you do. Never, never , never buy boots from a catalog - always go to a store and try them on with the socks you will wear while hiking.
In extremely cold weather I have yet to find a boot that is suitable for extended walking distances. The best I have found for combining warmth with comfort is the Acton military boot with the wool duffle liner. These things tend to be so roomy that your foot slides around inside the boot, and after a days hiking the soles of your feet become quite tender. This can be mititgated by running the laces through the loop on the heal of the boot, and while this does tend to keep your foot to the back of the boot, it is at best a medocre fix. One trick I have learned for cold weather hiking is to put a plastic shooping bag between two pairs of socks. This hold the moisture in the first sock, and prevents the sock from freezing to the bottom of the boot.