Pull the trigger. You want the Red Wings. My briar-brown chukkas are my go-to jeans shoes. They're going to take a bit to break in - and do your self the favor of not wearing them *every* day until they are - but they'll age very well.
The ideal fit I'm looking for once the boots stretch out and settle is a nice, firm fit (not tight) like a driving glove or a firm handshake with enough room to wiggle my toes without them being crowded. In order to end up in that desired fit zone, reason tells me that I'm going to have to buy boots that are going to feel tight and uncomfortable in the beginning. The $300 question is, how uncomfortable should they be in the beginning? For those of you who have achieved that firm, comfortable broken in fit, how much discomfort did you have to endure before you got there? Mild discomfort? Moderate discomfort? Verging on pain discomfort? I'll give them another try, but I seem to recall trying on an 11D and they pinched the top of my foot to the point of being painful after only a couple of minutes wear. My next step is to try on and compare an 11.5D and an 11.5EE. I just need to decide how much discomfort I might anticipate feeling with the expectation that they will loosen up and be comfortable once they stretch out. What was your experience?
I also wear muleskinner IRs, and have for over a year. The Red Wing water protection spray is the only protection I've given them. I've applied it twice. I only wear them urban hiking on my train/bus commuting and walking day in a somewhat wet environment (Seattle), but they are still awesome looking. I use a touch of Obenauf LP on my other IR and White's boots, but I would stick with the Red Wing water protection for muleskinners, unless you actually "work" in your boots.