An interesting question. I'm not tied to a specific handgun for carry, but I think it's most important to try to carry in the same type of holster, with the same cant, worn in the same place (and be practiced with one's drawstroke) as often as possible ... Hence, all my holsters for each handgun I may carry, are the same type of OWB or IWB.
Also, I may vary my carry gun, but I generally stick with similar platforms and keep aware of what I'm carrying.
I don't believe in changing guns for the season or for the type of attire ... more of a mood thing with me. Most often a Commander-sized 1911 (LW, Combat Commander, one of the Springer Champions or a Kimber Pro) ... but frequently a full-size 1911 1911 purists may be shocked, but I'll sometimes actually carry a [3"] Micro-Compact (which, amazingly, is totally reliable) for a change.
When the old-school feeling hits, I break out 4" S&W Model 19. Just 'cause it's pretty and brings back memories, kinda like running in to your high-school crush on a visit back to your hometown after a few years ...
And if I just want to have a buttload of rounds on tap, a W. German SIG P-228 w/two spare mags. Finally, an Airweight J-frame in the pocket for yard/garage work.