This getup shows it pays to invest in such timeless menswear pieces as a blazer and a sweater vest. This ensemble is completed nicely with dark brown leather derby shoes. In the winter months, when comfort is top priority, it can be easy to surrender to a less-than-stylish ensemble in the name of practicality. However, this ensemble is a striking illustration that you totally can stay snug and remain stylish during the winter months. Sartorial inspiration like this will help you stay enviously fashionable well into your 40s.