If you don't like spending too much time on your getups, opt for a navy turtleneck and grey plaid chinos. To add a little depth to this outfit, introduce a pair of black leather chelsea boots to the mix. When you have one of those bleak fall days, sometimes only a killer ensemble like this one can get you to face the outside world. Nice and age-appropriate for a 20-something man, an outfit like this will help outshine any of your fellows.