This off-duty combo of a long sleeve shirt and black ripped skinny jeans is a fail-safe option when you need to look cool but have zero time. And if you wish to immediately spruce up your ensemble with shoes, complete this ensemble with low top sneakers. Dressing smartly is the key to surviving below-freezing temperatures, but this getup is a vivid example that this can also be done with style. Wondering how to master casual outfits as you work your way through your 20s? This pairing is the perfect answer.