This outfit with a white crew-neck t-shirt and black chinos isn't hard to pull off and is open to more creative experimentation. Let's make a bit more effort now and complement your ensemble with a pair of monks. While dressing for winter can be a bit challenging, it's looks like this that make you feel excited. As a 30-something Millennial gent, you want to start dressing more professionally. That's when combos like this are a foolproof option.