Opt for a henley shirt and navy jeans to flaunt your styling smarts. Here's how to play it up: brown chelsea boots. During the colder months, when warmth is top priority, it can be easy to surrender to a less-than-stylish ensemble. However, this ensemble is a bright example that you can actually stay snug and remain stylish at the same time during the colder months. When it comes to dressing ideas for men over 30, this combination is a good look on most gents.