For a look that's nothing less than GQ-worthy, consider teaming a dress shirt with black and white dress pants. Hesitant about how to finish? Introduce a pair of black leather derby shoes to the equation for a more laid-back touch. Seeing as temps are dropping, this outfit seems a wonderful idea for the transitional season. That's the style for a gent in his 20s to project you've got what it takes to go places.