To assemble a relaxed casual ensemble with a modern twist, choose a charcoal crew-neck t-shirt and charcoal wool chinos. You can take a classic approach with footwear and complement your look with a pair of desert boots. While it can be tricky to stay on-trend on extra cold days, it's getups like this that prove it's quite doable. Overall, a perfect example of casual fashion for 30-something Millennial gentlemen.