Jan 21, 2014 Taylor Swift's Stylish Tomboy Look by Jessica Baker Free People Patton Pork Pie Hat ($58) MiH The Long Sportswear Cardigan ($86) Cooperative shorts Dolce & Gabbana Sara Pebbled Frame Shoulder Bag ($2295) Frye Courtney Boots ($288) Similar Styles: Express High Rise Cut Off Shorts ($50) Free People Patton Pork Pie Hat $58 Shop Now MiH The Long Sportswear Cardigan $86 Shop Now Dolce & Gabbana Sara Pebbled Frame Shoulder Bag $2295 Shop Now Frye Courtney Boots $288 Shop Now Express High Rise Cut Off Shorts $50 Shop Now Explore More: Celebrity Style