For a surefire classic and casual option, you can never go wrong with this combo of a grey wool blazer and navy jeans. Unimpressed with this outfit? Enter a pair of white leather oxford shoes to shake things up. During the winter months, when warmth is key, it can be easy to surrender to a less-than-stylish ensemble in the name of convenience. But this ensemble is a striking example that you can actually stay cozy and remain stylish during the winter months. This outfit demonstrates that staying fashionable as a middle-aged gent is totally doable.