Originally Posted by Englandmj7
True; I only wear slim jeans (Nudie SJs, etc.) and all of them are around an 8.5" opening, even then I would like them to be a little more tapered. My old gap bootcut jeans, or my friends that wear Sevens for instance (yes, I know, they shouldn't be my friends) have at least a 10" opening and look absurd with a nice pair of loafers or oxfords; they drag on the ground and cover up half the shoe. I don't know what kind of bootcut jeans these other guys think I am on about, but I am very close to posting comparison pics.....
First of all, I personally think that dressier shoes than, say, Paul Smith's distressed tan suede brogues look a little odd with jeans of any stripe. Having said that, I think that a lot depends on the size of your feet and how slim the shoes are. I thought that I had pretty average sized feet, US size 11, (or size 44.5 for all you Europeans,) but apparently, I have large feet, and favor a slightly elongated chisel toe or a round toe (like the casual shoes John Varvatos favors), so all except for the largest (10" +) openings are fine. On the other hand, if you are say, a size 8, and favor a Berluti like shoe, you had better go with a pretty small leg opening - I'd say that something like the HL classic (about a 8.2" opening, IRRC) would be better. It goes without saying that in any case, jeans should be slim at the thighs for this to look right in any case. An anti-fit or loose fitting jean, which is perfect for a slightly slouchy look with kicks and hoodies, doesn't work so well with brogues and a button-down.
And of course, boots (anything from Clarks desert boots to chelsea boots) look good with slim bootcut jeans, for obvious reasons. Again, imo, mileage varies depending on your shoe size.