I used to carry quite a bit for dressier low risk outings, my NAA Mini in 22 lr
then I bought an old S&W #1.5 spur trigger top break 32 S&W, that was chopped to a snubbie before I bought it... I liked carrying that & made a custom holster for it... at this time I also often carried an old Hopkins & Allen Safety Police top break DAO factory snubbie in 32 S&W
then I bought a S&W #2 spur trigger top break in 38 S&W & chopped the barrel to match my lil 32, & made a custom holster for it... this became my everyday gun for quite a while ( in fact I used this to re-qualify for my CCW this last time )
now my everyday carry gun is a custom Ruger Montado in 45 Colt... barrel is chopped to 2", & it wears a stainless birdshead grip frame with a set of checkered buffalo horn grip panels... it rides in a custom holster too
biggest guns were still snubbies, my custom Dan Wesson 44 Magnum, & my Ruger Alaskan in 454 Casull have both been on my belt since I got my CCW... but I tend towards lighter weight guns, & don't carry either very often...
the only autos to make the belt have been a Taurus TCP in 380, my CZ 75 Compact in 9mm, or my CZ Clone in 10 mm
been planning on my 5.7 X 28, but don't have a holster for that one yet...