For a look that's absolutely GQ-worthy, wear a navy and white dress shirt with a navy overcoat. To infuse a playful vibe into your look, introduce casual boots to the mix. If you're looking to stay warm this winter and look stylish while doing so, this look is your primary inspiration. After 30, you probably want to start dressing in a more sophisticated manner. If that's the case, ensembles like this are ideal as inspiration.