If it's ease and practicality that you're looking for in menswear, reach for a black hoodie and chinos. A pair of black leather chelsea boots easily kicks up the classy factor of any ensemble. In the winter season, when warmth is essential, it can be easy to settle for a less-than-stylish outfit in the name of functionality. However, this outfit is a striking illustration that you can actually stay toasty and remain equally stylish in the winter season. So if you're hunting for style inspo for dressing as you pass the big three-oh, this getup is a good example.