One of the best ways for a man to style out such a hard-working piece as a grey plaid double breasted blazer is to team it with jeans. For a sleeker twist, why not complete your getup with dark brown loafers? It's a savvy option when it comes to putting together a knockout outfit for awkward transition weather. Guys who wonder how to stay fashionable as you slip into your 50s, you have your answer.