When the situation calls for a casually smart ensemble, make a raincoat and a navy blazer your outfit choice. To introduce a bit of classiness to your outfit, complete your getup with a pair of burgundy leather double monks. There's no nicer way to brighten up a bleak fall afternoon than a sharp outfit like this one. As you're moving through your late 20s, you want to start dressing with more polish. In this case, outfits like this come in very handy.