A black shearling jacket and grey chinos will give off this relaxed and dapper vibe. If you need to instantly dress down this getup with one single piece, add white leather low top sneakers to the mix. During the winter season, when functionality is above all, it can be easy to settle for a less-than-stylish getup. However, this getup is a vivid example that you totally can stay toasty and remain stylish at the same time in the winter season. And if we're talking casual dressing ideas for men in their thirties, this combination is a good look on most guys.