Is that Harris Tweed? Looks nice. You are going to want to keep that clean.
If you decide to go with a short length, my only suggestion is to have at least an extra six inches so you have enough length to grip onto when you pull it tight. You can always cut it shorter, not longer.
I went with the Pendle and the Nelson Long Flap saddle bags in part because I thought that the leather patch would work better for me than the D rings. The D rings will let things flop around a bit more.
Just an FYI, I wanted my bags to have a better shape when part empty instead of hanging down like a one third full sack. I first tried some cardboard to see if it would work well as a stiffener, worked great. I replaced the cardboard with Coroplast so that it would work well if it got wet. Just a single piece bent into a U shape, not attached to the bag, just shoved into it, photo below.
Thus, my bags have a shape like below, even when empty. I do not like the bag hitting my legs as I pedal, so I used a stem with appropriate shim to push the bag further back. Photo below is on a different bike than my previous post.