If you're all about feeling comfortable when it comes to your personal style, this combination of a black bomber jacket and black and white sweatpants is right what you need. The whole getup comes together brilliantly when you complete your outfit with a pair of white and red leather low top sneakers. So if you're on a mission for an outfit that's seriously stylish but also feels totally season-appropriate, this one fits the bill. Now that's how you dress casually at 20.