This look with a light blue dress shirt and navy jeans isn't so hard to score and easy to adapt. A pair of boat shoes immediately amps up the wow factor of this outfit. So as you can see, this outfit is a really good option, especially for summer-to-fall weather, when the temperatures are getting lower. Just because you've reached your 40s, doesn't mean you're allowed to give up on fashion, and this outfit illustrates exactly that.