This off-duty combo of a dark green shirt jacket and jeans can only be described as seriously sharp. If in doubt as to what to wear when it comes to shoes, stick to brown leather desert boots. During the winter season, when warmth is top priority, it can be easy to surrender to a less-than-stylish look. This look, however, is a striking illustration that you totally can stay comfortable and remain stylish during the winter season. Wondering what to wear as you move into your 30s? This combo is a practical example.