Jessica S. can often be spotted in the South End soaking up arts and culture events. This time, I found her while she was out walking Oscar, her cute Wheaton Terrier. Jessica's outfit is a great example of stylish weekend style: cute and versatile layers matched with hip accessories. Jessica says she builds her winter looks by buying comfortable wardrobe staples like the kind she's been craving lately: "cozy sweaters, scarves, slouchy hats, and skinny jeans." Jessica's hat is from H&M, her glasses are from 9Five, her hoodie is from Allsaints, her leather jacket is from Anthropologie, her jeans are from BDG, and her boots are Frye.