Such items as a dark green blazer and navy ripped jeans are an easy way to introduce some cool into your daily rotation. You can get a little creative when it comes to footwear and elevate your getup by slipping into dark brown leather chelsea boots. As you can see here, it's super easy to look awesome and stay cozy when chillier weather comes, thanks to this outfit. Those who are curious whether you can still pull off modern casual dressing well into your 50s, you have your answer.