This smart casual combo of a dark green polo and dark green dress pants is extremely easy to pull together in seconds time, helping you look awesome and prepared for anything without spending a ton of time searching through your wardrobe. When in doubt as to what to wear when it comes to shoes, introduce a pair of chelsea boots to the equation. It's is an appealing idea when it comes to a kick-ass summer-to-fall look. As you're moving through your late 20s, you probably want to start dressing more maturely. In this case, outfits like this are a winning option.