For a dapper ensemble without the need to sacrifice on practicality, we love this pairing of a tan barn jacket and a brown turtleneck. A pair of brown leather desert boots finishes off this outfit quite nicely. There's no nicer way to spice up a gloomy fall afternoon than a cool look like this one. It often pays to break out of your style comfort zone as a 20-something and move into a fancier one.