Flannel shirts can look like a lumberjack, but they can also be perfectly preppy (yet still cozy) when worn right! I love the look under a puffer vest or with jeans little wedge booties. This is the perfect outfit to wear to class or running errands, because you can make it look pulled together, but it doesn't look like you are trying too hard.
This one is on sale at J.Crew.
Get the look: