I hike in barely over the ankle "bootlets" and my husband hikes in full boots. I really think what you wear hiking has to do with two main points:

1. Terrain - we have, what my husband has named, Tundra Tuff... weird spongy stuff, at least if you are off trail. They really recommend over the ankle boots for hiking this stuff.

2. what you wear normally - I wear tennis shoes to work, and my husband wears boots. His biggest issue with breaking in new boots is they always hit in a different spot on his calfs than whatever he wore previously, drives him nutz for a week or two.

I think he needs new hiking boots and will send your recommendation on to him. =)