Such pieces as a red and navy short sleeve shirt and skinny jeans are an easy way to infuse understated dapperness into your current casual routine. To bring a little zing to this look, grab a pair of silver leather chelsea boots. And if you're in search of a cool outfit that will take you from winter to spring, this one fits the task well. Gents wondering how to dress well and look good in your late 20s, you have your answer.