If you prefer comfort dressing, why not try this combination of a hoodie and black skinny jeans? If you want to easily amp up your outfit with one single item, complete this ensemble with tan suede chelsea boots. During winter, when warmth is essential, it can be easy to surrender to a less-than-stylish look in the name of practicality. But this look is a clear example that you totally can stay comfortable and remain stylish at the same time during winter. Men wondering how to look fashionable in your early 20s, you have your answer.