This combo of a red and black long sleeve shirt and light blue ripped jeans is proof that a safe casual look doesn't have to be boring. When it comes to shoes, this ensemble is completed really well with high top sneakers. Dressing smartly is the trick to surviving cold temps, but this outfit is a practical illustration that you can accomplish this with style. Those who wonder how to sport modern off-duty outfits as you work your way through your 20s, you have your answer.