I'd agree that wingtips go well with both broad categories of toes. However, I think jcusey is on to something because there are "round" toed lasts that are so sleek and bullet nosed that I think a very sleek wingtip makes them look TOO bullet-nosed. C&J 363 might be an example of such a last.
While smart round toes do look good with a robust wingtip, as with G&G's here:
I think a really refined and sleek wingtip like an austerity starts to look TOO bullet-nosed on a smart round (here AE's 8 last):
Even more so on a round needle toe, like this one I ripped from Istvan Toth of Budapest.
See how the stitch cap saves it and gives it some perpendicular interest?
I ordered an austerity wingtip in something very like the AE 8 last, and while it's definitely a good looking boot, there's something just a little TOO bullet-nosed to it. Imagine this St. Crispin's all in dark brown calf:
The suede saves this one, but in dark calf of the same tone, there'd be no centrifugal pressure to counterbalance the backward thrust of the wingtip on that last.
Edited by Testudo_Aubreii - 1/23/16 at 6:09pm