If you gravitate towards comfort dressing, why not take this combination of a grey v-neck t-shirt and cargo pants for a spin? If you want to effortlessly step up your ensemble with shoes, add beige suede chelsea boots to the equation. It's a nice idea when it comes to crafting a well-coordinated outfit for transeasonal weather. Guys who are curious how to sport cool casual looks as you turn 30, this getup should answer your question.