If you can’t already tell, I really document my casual outfits. At one end, I typically dress down a suit or blazer with a polo shirt. For the other side of the spectrum, I go full 1990’s inspired, with a faded sweater and some jeans and sneakers. For this article, I decided to delve more into into an outfit that is more “casually tailored”, a term frequented by style bloggers like Dan Trepanier. My version looks toward the cool summer/vacation styles of the 1930s-1950s, where tucked in shortsleeves were all the rage. It’s perfect for summer, since you’re probably looking to leave your long-sleeve shirts at home.