Marry a grey vertical striped short sleeve shirt with navy jeans to feel self-confident and look casually dapper. Complete your ensemble with dark brown leather casual boots for an air of sophistication. Picking out a well-coordinated combination can be a bit of a juggling act on its own. Enter extra cold temps into the equation, and the whole thing becomes even more difficult. Luckily, this here is your wintry inspo. So if you're searching for dressing tips for 30-something guys, this outfit is perfect.