A red long sleeve shirt and light blue ripped jeans have become a favorite casual pairing for many fashionable men. If you're clueless about how to round off, introduce a pair of high top sneakers to the mix. In winter, when warmth is the priority, it can be easy to settle for a less-than-stylish outfit in the name of practicality. However, this outfit is a shining example that you can actually stay toasty and remain equally stylish during winter. Those who wonder how to dress well and look good as you work your way through your 20s, you have your answer.