What: The Boyfriend Shirt
Where: American Eagle Outfitters (various locations)
Price Tag: $39.95
Why: A good denim shirt is one of only a few fashion items that transcend all genres. Think about some of the style icons who’ve rocked one: Bob Dylan, James Dean, Brigitte Bardot, Kate Moss, Kanye West… You get the picture. This soft chambray version is a beautiful faded-blue hue, and it has faux pearl snaps and a curved hem that looks super flattering when left untucked. Try wearing it tucked into white jeans with leopard-print flats, or leave it loose with black skinnies and Birkenstocks. Make sure the sleeves are rolled for that perfect “I tried, but not that hard” look.