Miley Cyrus Wearing Ripped Boyfriend Jeans

Miley Cyrus excels at the art of unexpected fashion pairings, working retro dresses with high-top sneakers, short shorts with knee-high boots, and now, distressed boyfriend Levi's jeans with tan peep-toe Elizabeth and James wedges ($275). Miley played with proportions in a cropped white tank and oatmeal cardigan, then took her stellar Philadelphia style a step further with a black studded Valentino bag ($1,598), a bevy of gold accessories, and round tortoise shades. Copy this downtown-cool style with distressed denim, a cropped tank and cardigan, and leather peep-toe wedges for a shopping date with the girls.