Ashlee Simpson-Wentz isn’t the type of gal I’d typically expect to see wearing a blue and white checked dress, but there’s nothing wrong with getting your Dorothy on. The singer gives her frock an edgy twist by pairing it with black tights, booties, and an enticing ruched Chanel purse. I’m not 100% certain that everything flows, but it’s hard to find much fault with Chanel. What do you think?

Photo from GlamourMagazine.co.uk