A lot goes into such choices. Initially there's personal experience with a given system, budget, and perceived needs. That influences what guns a person ends up owning. There's also differences in local laws (such as mag capacity limits in some states) and flora and fauna (man eating critters in some states, or the ever present danger of being Bigfoot's forest bride) vary from region to region.

Thus - what do I have, how well do I know how to use, and what is it for/going to be used for are as much deciding factors as how it is to be carried and whether or not it matches the day's outfit.

Lately I've liked my Sig P229R in .357 Sig. In VA (I'm now in SC), .357 Sig JHPs were the only defensive loads that I could reliably find. The gun has night sights which I like, and offers a reasonable balance of carry convenience, power, and capacity. I tend to always carry one or more J frame .38s and generally keep a pile of spare .38s around.

I actually prefer SA autos, but I don't feel like wearing out my old Colt 1911 which is less expendable.