Warm weather, light clothing-Ruger LCP in DeSantis Super Fly pocket holster
Cooler weather with more covering clothing-SA XD40 Subcompact in JMG IWB 3.2 holster.
Warmer weather: Ruger SP101 3 1/16" in .357 magnum, carried in a Crossbreed Supertuck.
Colder Weather: Sig Revolution TTT Fullsize 1911 in a pancake holster.
I always carry at least one extra magazine with the 1911, usually two. At least two HKS Speedloaders always ride along with the Ruger and I.