To look like a stylish dandy at all times, consider pairing a black shirt jacket with grey dress pants. If you're puzzled as to how to finish off, add brown suede derby shoes to the mix. Can you see how extremely easy it is to look stylish and stay warm when cooler days are here, all thanks to combos like this one? That's the look for a 20-something guy to portray he has what it takes to go places.