Jill has to be one of our most interesting Advanced Style Subjects to date. She looks so pretty and true to her California roots in her Guatemalan worry doll hat and wonderfully colorful dress and coat. After meeting Jill, however, it became clear that her sense of adventure is definitely not limited to style: she told us that for her 80th Birthday, when she was in Vegas with her son, she became the oldest person to go Bungee Jumping! Check out the video of her jump, below… Amazing!

She also told us about her work with the Pancreatic Cancer Action Network, her time modeling eyes, legs, and hands in New York, and her memories of an undeveloped San Diego when she was a girl. Jill will be 85 this year, and she is still stylish, energetic, and making the most of life. What a great Advanced Style icon.

Yesterday, I was lucky enough to see Tony Bennett walking on the street close to Central Park with a friend. From the look of their bags they’d just come from MoMA, and they seemed in a great mood. He looks handsome as always, and I love how he’s paired a light blazer with dark blue slacks. His friend’s muted grey and black Hawaiian shirt is very cool, and happens to complement the colors in the picture very well! Come to think of it, Bennett might be a great addition to my Fall playlist…

This adorable couple, visiting New York from their home in England, exudes happiness and great attitude. When we met them, they were strolling down the streets of the West Village with their son and granddaughter, enjoying a sunny Autumn day. It’s always impressive to see such stylish travelers, even when you know they’ve only got a suitcase of things to choose from. We hope they enjoy the rest of their trip.

Ari and I have been complaining about the lack of color in Fall, but this woman has found a great way to embrace the season without losing some zest in her color choices. Her bright orange bag complements the darker, muted colors of Fall that she’s wearing, and she looks perfect for harvest time. Her tipped-back hat adds that touch of distinctive arty cool.