I agree with this. RLH will be well suited to wear with shorts. Yes, in fact I have a Ranger Moc with a midsole and a suede chukka with a midsole. Seems to be standard issue with the RLH and the crepe outsoles. Both look more or less like this (I know I keep reposting this photo, but it seems pertinent to the topic at hand...) I'm not sure the midsole really adds anything extra to the support and comfort. In fact, on one or two descriptions on the Rancourt site, I've seen the phrase "aesthetic leather midsole," which leads me to believe it's not doing much of anything at all. Not sure if some are aesthetic and others functional or what. And sorry. I didn't realize you were one of our antipodean friends. The fit program probably isn't quite as useful then. I will say that the lined suede chukka I have in 11D (my technical true size, though I am a border line E width it seems) is snug. It's fine sockless, after a short break-in period, and I can wear it with thing socks, but anything too much and it gets to be a tight squeeze. Which is to say that I think your fears about 9D lined Ranger Moc may have some foundation. Going out a width is an option since you will be able to lace these up and you could always add a tongue pad or thing insole to take up any slight excess in room. I have a pair of 11E beefroll loafers and I use a tongue pad in them. That might be your best bet since the length is already good and going up .5 size to get more room might change the fit there for the worse (and I think would end up giving you essentially 9E in width anyway, if you see. That may be a little too simplistic, but I think it is about right). They do have lasts with differences in fit (loafer vs. lace-up), but that may be introducing one too many variables.