This combination of a black shearling jacket and black chinos is the perfect base for a casually stylish look. Complete this ensemble with black leather low top sneakers to inject a hint of stylish effortlessness into your look. With an ensemble like this in your winter collection, you're guaranteed to stay snug and look stylish despite the below-freezing temperatures. Those wondering how to dress stylishly as you slip into your 30s, you have your answer.