Well, I'll normally try for bigger width since there's more options to make it fit than wearing a size smaller shoe (generally means you need to stretch them out by a bigger shoe tree or using alcohol to loosen up the leather for it to stretch with a shoe stretcher [last resort option; not recommended unless you willing to throw the shoes away])
Shoe's proportion might not look nice after a forced stretch normally or with wrinkles at the wrong place. If difference is lesser than half size then maybe the leather will seasoned to your size.
Unfortunately the 5 last is quite tricky for some people but I have no issues going with my brannock sizing which is 8.5D. Surprisingly, I had issues with last 7 though for their MacNeil as the toe box was not as generous as I thought due to the sharper converging toe when I sized down to 8D. Not sure if that helps