This pairing of a grey vertical striped dress shirt and black wool dress pants is a fail-safe option when you need to look seriously stylish and elegant. Introduce black leather loafers to the equation and the whole look will come together quite nicely. So when summer is fading away and fall is in the air, you'll find this ensemble to be your everything. And if we're talking fashion for 30-year-old guys, this combination is a good look on most gentlemen.