If you feel more confident in comfortable clothes, you'll appreciate this relaxed pairing of a white and red short sleeve shirt and jeans. Not sure how to round off this getup? Round off with tan suede chelsea boots to bump it up a notch. When leaves turn yellow and red and autumn takes over, you'll love this combo as your go-to for awkward fall weather. And if we're talking fashion for men over 40, this outfit looks good on almost any gent.