Street View is a fashion series in which Isa Giallorenzo spotlights some of the coolest styles seen in Chicago.

Guess who I ran into again? Sandra, my ultimate style icon, who was featured in one of my early Street Views. This very fine lady always amazes me. How can someone look so age-appropriate, chic, fun, and on-trend at the same time? I also love the fact that she’s incredibly cool, but always manages to make a fashion statement. Sandra once gave me the best tip ever: keep your hair long if you don’t have the time or money to properly maintain it. She firmly told me, “Don’t go to a hairdresser for two years!” This piece of advice made me a new, more polished, and less broke woman. Sandra is usually rocking her long luscious white hair in a charming side ponytail or in a casual chignon. Another perk of catching up with her is that she’s basically a walking encyclopedia of Chicago’s fashion history. Her Armani jacket, for example, was bought at the legendary (and now defunct) Oak Street shop Ultimo, formerly owned by equally legendary Joan Weinstein. According to Sandra, Prada used to suck until Joan Weinstein went to work for the brand. Now you know.

See a few shots I took of Sandra for this Korean magazine after the jump.

Below are some pics from a photoshoot we did for Cracker Your Wardrobe (yes, Cracker!):

See more Chicago street style in the Chicago Looks blog.