Consider pairing a brown overcoat with charcoal wool dress pants and you're bound to make an entrance. Feeling creative? Tone down your getup by slipping into a pair of dark brown leather desert boots. In winter, when warmth is the priority, it can be easy to surrender to a less-than-stylish outfit. But this outfit is a bright example that you can actually stay comfortable and remain stylish at the same time during winter. This pairing illustrates that figuring out fashion over 50 is quite manageable.