In other words, you don’t need a boarding school background ... polished and preppy looks go, you can’t go wrong with a cashmere tee like this relaxed piece from J.Crew. It has a shorter ...

Available in eight background colors, this unisex tee is made from cotton for a comfy, breathable fit. This cozy hoodie has an uplifting message (and another smiley face for extra preppy points).