I am very, very picky about my shoes. I agree that it's difficult to find comfortable yet stylish shoes. So far, what I love and what works for me is
COLE HAAN with NIKE AIR Technology. Compared to the other brands, Cole Haan has everything from sandals, flats, wedges, high heels & boots (all with Nike Air Technology), and with pretty designs to choose from. The collaboration with Maria Sharapova has really improved their line. As a testament to how comfortable and stylish their shoes are, Angelina Jolie wore the shoes for red carpet events while she was preggers!
Don't know how to insert photos, but here are links of samples:
1. CH Flats with Nike Air -
http://www.colehaan.com/colehaan/cat...EN%27S|BALLETS
2. CH Wedges with Nike Air -
http://www.colehaan.com/colehaan/cat...N'S|WEDGES
3. CH Pumps / Heels with Nike Air -
http://www.colehaan.com/colehaan/cat...OMEN%27S|HEELS
4. CH Boots with Nike Air -
http://www.colehaan.com/colehaan/cat...OMEN%27S|BOOTS
Other shoes you may want to look at are
Naturalizer and
Aerosoles. They are comfortable, and designs are relatively okay.