For an off-duty outfit, marry a hoodie with jeans — these pieces go really good together. Here's how to dial down this look: beige snow boots. During the winter months, when functionality is imperative, it can be easy to surrender to a less-than-stylish ensemble. This ensemble, however, is hard proof that you totally can stay toasty and remain stylish during the winter months. A cool, less conservative ensemble for 50-year-old gents.