This classy combo of a white dress shirt and a grey suit is a frequent choice among the fashion-savvy chaps. For a more casual vibe, introduce navy leather low top sneakers to the equation. Can you see how super easy it is to look dapper and stay toasty when chillier weather hits, all thanks to outfits like this? Wondering how you should dress as you work your way through your 20s? This pairing is the perfect answer.