This combination of a navy suit and a white and navy gingham dress shirt is a winning option when you need to look sophisticated and really sharp. Our favorite of a myriad of ways to complement this ensemble is a pair of black leather loafers. As you can see here, this look is a really savvy idea, especially for in-between weather, when the mercury is dropping. This outfit demonstrates how to score in semi-casual dressing as a 20-something guy.