Demonstrate your expertise in menswear styling in this relaxed casual pairing of a v-neck sweater and black skinny jeans. Balance this outfit with more casual shoes, like these tan suede work boots. During the winter season, when functionality is everything, it can be easy to settle for a less-than-stylish outfit. This outfit, however, is a striking example that you can actually stay snug and remain equally stylish in the winter season. All in all, a nice option if we're talking style for over-30 guys.