Wear a crew-neck t-shirt and beige chinos to put together a laid-back and cool look. Up the classiness of your outfit a bit by slipping into dark brown loafers. While it can be a bit of a juggling act to look stylish on extra cold days, it's combinations like this that prove it's quite doable. As you slip into your 30s, you probably want to start dressing more like a mature gentleman. In this case, inspo like this comes in very useful.