If you enjoy the comfort look, consider teaming a red and black gingham long sleeve shirt with black chinos. For something more on the smart side to finish your look, complete this getup with a pair of black leather dress boots. As you can see here, it's extremely easy to look dapper and stay toasty when colder weather hits, all thanks to getups like this. On a mission for style tips for 20-year-old guys? This ensemble is pretty inspiring.