I think if 'twere I making the choice, and I knew that I would be wearing tall boots, I would want long socks between the leather and my leg-flesh. And, if I were wearing tall boots that were strapped to said leg-flesh with multiple lacings, I wouldn't worry about what was holding up the socks because the lacings of the boot would be tight enough to do the job. However, since my feet sweat like a son-of-a-gun and the thought of being bound up in leather boots gives me the willies, I think I'll stick my my Keens.

To the OP:
For Ren Faire, I think the shoes you pictured (the "Gaelles") look better than the tall boots. What kind of sole do they have?