A modern gentleman's classy wardrobe should always include such essentials as a dark brown plaid blazer and charcoal dress pants. Give a dressed-down twist to an otherwise mostly classic ensemble with dark brown suede desert boots. In winter, when comfort is the priority, it can be easy to surrender to a less-than-stylish outfit. But this outfit is a vivid example that you can actually stay comfy and remain equally stylish in winter. This getup illustrates that in your thirties your styling options are pretty much limitless.