I love the idea of a tailored jacket with sportier shorts.
Two years ago I tried a few very casual, unconstructed cotton sport coats (45RPM, Junya, and Engineered Garments to be exact) but the lack of structure and sculpting in the high-waist made the look too shapeless for my tastes.
I’m not saying that the option above is the perfect scenario, but it’s a very good reference point.
Actually, last week in Milan I found a great cotton sport coat at Piombo. The jacket fits like the one above, but the upper-sleeve is slimmer and the washed cotton gives the jacket a sportier feel.
I have to write more about Piombo later. If you don’t know it, imagine an Italian, super chic version of J.Crew.