Go for something comfortable yet modern in a white and black long sleeve shirt and light blue ripped jeans. High top sneakers act as the glue that will bring this getup together. While it can be a bit difficult at times to stay fashionable in below-freezing temperatures, it's outfits like this that prove it's totally possible. Gents who are curious how to rock modern off-duty dressing as you cruise through your 20s, this getup should answer your question.