For an outfit that's casually sleek and gasp-worthy, try teaming an overcoat with jeans. Our favorite of an infinite number of ways to finish this outfit is with a pair of brown leather work boots. During winter, when warmth is imperative, it can be easy to surrender to a less-than-stylish look. But this look is a bright example that you totally can stay comfortable and remain equally stylish during winter. All in all, an ideal example of off-duty fashion for over-30 guys.