My Chippewa snake boots are workhorses, because they were designed for physical work. However, I get so many compliments on how cute the boots are that I often reach for them for style reasons alone. They're that rare breed of footwear that functions well, looks good, and has arch support+ comfortable padding for the soles.
Ariat does really well at the same thing: function, comfort, style.
I've had good luck with Cole Haan. Some of their shoes have Nike air tech in them.
Naya does a good job of combining comfort and style. I have some sandals from them that have great arch support.
OTBT does some comfortable and cute footwear. I don't get all of the arch support I like from the shoes I've had from them, but they don't hurt my feet at least.
Last but definitely not least, for me personally, are my Bates tactical boots. They're a combat style boot made for professionals (cops, firefighters, EMT personnel, etc), so they work for my RATE sensibilities and give me all-day-long comfort at my work. I don't know what the rest of their product line looks like, so I don't know if they make anything that would be considered cute or stylish for non-RATE style sensibilities, but I had to mention them for casual wear simply because they really are comfortable for the entire 10 or 11 hours I'm on my feet at work every Friday.
Honorable mention: my Vic Matie loafers. Comfortable enough that my feet don't hurt after a day of running errands and such.
