For a laid-back look, choose a red crew-neck t-shirt and grey chinos — these pieces work nicely together. Take an otherwise dressy outfit a whole other path by slipping into work boots. During the winter months, when warmth is top priority, it can be easy to surrender to a less-than-stylish getup in the name of convenience. However, this getup proves that you can actually stay comfy and remain equally stylish in the winter months.