This pairing of a black blazer and a white polo is a foolproof option when you need to look on-trend but have zero time to dress up. You can go down the casual route when it comes to footwear by wearing a pair of white canvas low top sneakers. In the winter months, when functionality is key, it can be easy to settle for a less-than-stylish look in the name of functionality. But this look is a vivid example that you can actually stay toasty and remain equally stylish in the winter months. Men wondering how to wear classic and casual looks as you move through your 20s, you have your answer.