Swing into something effortlessly elegant and trendy with a tan plaid blazer and a white and blue vertical striped dress shirt. To give this getup a classier touch, add a pair of brown leather tassel loafers to the mix. During the winter months, when warmth is a must, it can be easy to surrender to a less-than-stylish ensemble in the name of functionality. But this ensemble is a striking illustration that you can actually stay comfy and remain stylish at the same time during the winter months.