FIT
A perfect fit takes time to determine, and each brand will be slightly different. Try several models, and don't determine fit until the boot is laced correctly and you're standing up. Allow a little space for foot swelling and thicker socks.
ANKLE HEIGHT
Tall cuffs provide ankle and lower leg protection, but very tall cuffs might restrict agility. They also add weight and increase a boot's drying time. Boots with two sets of lace hooks in the cuff are a good mid-point option.
MIDSOLE
For longer trips on rough terrain, stiffer boots are preferred for protection and to prevent foot fatigue.