My Paul Green 'Jay' chelsea boots fit both criteria. Most of my footwear seems to lean more in one direction or the other but doesn't totally combine the two qualities. I seem to have a lot of shoes that are "just comfortable enough" and other shoes (my Dansko 'Ingrid' clogs) that are comfortable but not very appealing from a style point of view). I would like to gradually transition to shoes that combine both style and comfort and would love to hear about shoes/boots/sandals that strike this balance.