Pistols are becoming a classic, don't thing they will get out of style soon,
I'd get the givenchy shark boots, in leather, and i would get the saint laurent Debbie boots , they both not very practical ,but you said if money is no object
,ohh and I would throw in a few Rossi pairs.
On a more serious note, I have a few pairs of Marant shoes /boots and they are fab, very hard wearing, and another great boots,probably my best boots investment is the jimmy choo bikers,