Try teaming a dress shirt with charcoal jeans and you'll create a neat and elegant look. Introduce dark brown dress boots to the equation to instantly jazz up the look. You might be thinking that just because you need to get bundled up you have to sacrifice on style, but that's just not true, and this look is a bright example. As you're moving through your late 20s, you probably want to start dressing more like a mature gentleman. That's when getups like this are a safe option.