A tobacco shearling jacket and skinny jeans are a casual street style combo that every modern gentleman should have in his off-duty wardrobe. Puzzled as to how to finish? Complement this look with beige athletic shoes for a more relaxed aesthetic. With a look like this in your winter closet, you're guaranteed to stay comfy and look stylish despite the nasty weather. Those who are curious how to pull off cool off-duty dressing as you cruise through your 20s, you have your answer.