From a comfort perspective, I bought these after trying on a LOT of boots. They look similar to the jcrew ones.
http://www.zappos.com/sperry-top-sider-ambrose-black
They are comfortable for my average feet (size 7.5).
And yes, I thought I hated ankle boots too. They are kind of silly. But everyone has them, so I caved. I like them with jeans rolled up a bit.