A crew-neck t-shirt and skinny jeans are awesome menswear staples to add to your off-duty wardrobe. Channel your inner David Gandy and add a pair of black leather derby shoes to the equation. This one is a great option if you're figuring out a cool look for unpredictable fall weather. It often pays to step out of your style comfort zone as a teenage boy and take a step in a fancier direction.