If you're on a mission for a casual and at the same time sharp outfit, choose a varsity jacket and a black and white crew-neck t-shirt. To give your overall outfit a classier vibe, why not complete this getup with black leather chelsea boots? As you can see, it's very easy to look sharp and stay toasty when chillier weather hits, thanks to this look. If you're often not sure how to dress appropriately for your age while looking stylish, this ensemble is a perfect example.