For an outfit that's street-style-worthy and casually smart, rock a crew-neck t-shirt with charcoal vertical striped dress pants. If you wish to easily dress down your getup with one item, add grey athletic shoes to your ensemble. A cool getup that will take you from summer to fall like this one makes it very easy to embrace the new season. And if we're talking style for men in their 20s, this getup looks nice on most guys.