Wear a bomber jacket and grey wool dress pants - this look is guaranteed to make a bold statement. Introduce dark brown chelsea boots to the equation and you're all set looking smashing. As you can see, it's very easy to look amazing and stay snug come fall, all thanks to looks like this. As you mature into your 30s, you want to start dressing in a classier manner. In this case, outfits like this prove useful as a source of inspiration.