A dark brown bomber jacket and a black crew-neck t-shirt are a good pairing worth integrating into your current arsenal. Feel uninspired with this outfit? Enter a pair of black leather loafers to change things up a bit. So if you're searching for a look that's stylish but also totally season-appropriate, this is it. If you're often not sure how to dress appropriately for your age while looking stylish, this combination is a practical illustration.