Choose a grey blazer and navy jeans for a clean-cut elegant outfit. Make a bit more effort with footwear and complement your ensemble with a pair of black leather derby shoes. During winter, when warmth is everything, it can be easy to settle for a less-than-stylish outfit in the name of functionality. But this outfit is a striking illustration that you can actually stay snug and remain stylish in winter. As you're going from your 20s to your 30s, you want to start dressing more like a mature gentleman. If that's the case, getups like this are a fail-safe option.