Pair a red and navy crew-neck t-shirt with jeans to flaunt your styling skills. On the shoe front, go for something on the more elegant end of the spectrum and complement your outfit with a pair of brown suede casual boots. In the colder months, when functionality is top priority, it can be easy to settle for a less-than-stylish look. But this look is a vivid example that you can actually stay toasty and remain stylish at the same time during the colder months. Casual ensembles for men in their 30s aren't actually that hard, as you can see here.