We love how this smart casual combo of a tan trenchcoat and jeans immediately makes you look sharp. Balance out this ensemble with a more elegant kind of shoes, such as these tobacco double monks. Can you see how very easy it is to look dapper and stay comfy when cooler weather hits, thanks to this outfit? As you're progressing through your adolescence, you probably want to start dressing more maturely. In this case, inspiration like this comes in very handy.