Ive bought expensive shorts and they have lasted a good amount of time. I just tried on shorts after a long time and I tried a 9" and an 11" inseam. The 9" is way too short for my liking and the 11" was comfortable and what I ended up buying. I wish these were longer, I probably would have gotten the olive and maybe one more color.
Chestnut is a great 3 season color. I would wear in spring with worsted wool in lighter colors. Summer with linen would be a great combo. Fall chino or moleskin in lighter colors would be fantastic.
Some might wear tweed for winter but I prefer boots or heavy grain during that time.
Those are beautiful