To create a laid-back look with a modernized spin, wear a dress shirt and blue ripped jeans. And if you need to effortlessly level up this getup with shoes, why not complete your getup with a pair of tan desert boots? So as you can see, this look is a really wonderful pick, especially for awkward transition weather, when the mercury is starting to drop. This outfit demonstrates how to keep slaying in casual dressing as a middle-aged man.