Jen Brill- Classy and Sassy. Exemplified by her Burberry/leopard pairing and choice of reading material. A concise review of Derek Blasberg's book here. Photos via http://www.terrysdiary.com/
Imparting the walking advice that was bestowed upon me by my maternal elders (1) Walk only with a forward stare. If you're looking at others, they aren't look at you (2)Walk like you own the sidewalk and you will Nadia Cassini exemplifies this familial wisdom.