If you prefer off-duty looks, why not take this combo of a crew-neck t-shirt and beige chinos for a spin? Feeling transgressive today? Smarten up your ensemble with a pair of dark brown loafers. During the colder months, when comfort is prized, it can be easy to settle for a less-than-stylish outfit in the name of functionality. This outfit, however, is a striking illustration that you totally can stay snug and remain stylish at the same time in the colder months. This getup proves that figuring out how to dress stylishly as you mature into your 30s is easier than one might think.