Originally Posted by Roger
Well, I guess it remains for me to be the contrarian on this question. In my mind, most cap-toes, and particularly balmorals, just look out of place with anything remotely casual. The Mackay will look good with a suit, but a little less so with a sports jacket/odd trousers. Perfed bluchers would be fine in the latter case, but to my eye, sleek balmorals like these look badly incongruous with jeans, chinos, or, really, anything but a jacket and tie at least. The Barksdale, on the other hand, looks completely natural with jeans, chinos, and anything casual, but can, in addition, be appropriately worn with jacket/tie/odd trousers, and would look ideal with a jacket and turtleneck or jacket/open-collared shirt. Further, sleek, stylish, and high-end loafers like these can, if necessary, work with a suit too, not looking badly out of place.
This sums up my feelings, exactly. I'd wear the Barksdale with anything other than a suit (although there are better shoes for jeans, no question). I wouldn't wear the Mackay with anything but a suit or a jacket and odd trousers. For the record, I don't think the Barksdale (or loafers in general) are old-manish (although this is probably because I wear loafers all the time and I'm only 36). I'm actually wearing my Barksdales today, and I love them.
NMW1982 - you seem to be obsessing over this a bit too much. Both the Mackay and the Barksdale are excellent shoes from a quality standpoint. Go with the one that you like more. No one is going to criticize you for it, either way. Whichever you choose, you'll be wearing better shoes than 95% of the male population.