This relaxed casual combo of a crew-neck t-shirt and white chinos is a goofproof option when you need to look sharp but have no time. Balance out your getup with more laid-back footwear, such as this pair of tan suede work boots. In the winter months, when warmth is the priority, it can be easy to settle for a less-than-stylish look in the name of convenience. This look, however, is a stark illustration that you can actually stay comfy and remain stylish at the same time during the winter months. This one is a good-looking but also age-appropriate getup for 50-year-old guys.