So I just got a pair of Herring Shakespeare IIs in suede (pic below).
First impression out of the box was that they're very pointy in the toe. After wearing them for a day they don't seem so pointy anymore. FWIW, I've had this reaction to other shoes before--they seem weird looking at first, and then, after a short while, perfectly normal-looking.
Still, the last might be a little too elongated for jeans. Everything else about the shape is fine, great even, and the suede is a nice colour.
One other thing is that I'd prefer silvery buckles to brass-coloured ones. But this is of course minor.
I guess the obvious comparison with these is with C&J Lowndes. Would I love C&J Lowndes harder? Probably, everyone here loves C&J, I expect I'd be no different. But then, these are $300 shoes and C&Js are $400+ ($500 locally here in Oz), I'm no baller, and suede is suede. At the end of the day, I expect to be wearing these with pleasure for years to come.