You totally wish you knew Jessie Artigue. Not only is she a professional stylist, a go-to trend-reporting source for major media outlets, a trained journalist, and a personal fashion-advice swami, she's also got top taste in nibbles and drinks. Imagine strolling down the sidewalks with her as she helps you re-imagine your wardrobe. After some noontime shopping at her favorite store, you head to a cute little bar before she stops mid-sentence to snap a street-style pic for her blog, Style and Pepper. Sounds pretty idyllic, right? Well, even though we can't introduce you to her directly, we're giving you the next best thing — a virtual afternoon downtown with Jessie as she clips along in her Clarks, takes you to her favorite spots, shows you what she packs in her purse, and offers you her definition of good street style.
Photographed by Aaron Richter, Styled by Claudia Cifu, Hair by Sera Sloane Bishop, Makeup by Tiffany Patton.