This combo of a white dress shirt and light blue jeans is undeniable proof that a simple off-duty look doesn't have to be boring. Add black leather ankle boots to the mix and ta-da: the ensemble is complete. During the winter months, when practicality is critical, it can be easy to surrender to a less-than-stylish outfit in the name of convenience. But this outfit is a striking example that you can actually stay toasty and remain equally stylish in the winter months.