Go for a simple but polished choice by pairing a grey overcoat and charcoal jeans. Dial up the fashion factor of this look with dress boots. During the winter season, when practicality is key, it can be easy to surrender to a less-than-stylish look in the name of convenience. However, this look is a shining example that you totally can stay snug and remain stylish at the same time during the winter season. Interested in style tips for 20-something gentlemen? This ensemble is pretty inspiring.