It might have been out of fashion after 1914 for a clean cut cowboy but when you look at true 19th century photos of working cowboys, wearing pants inside the boots was the norm and it actually still is today if you go to a farm or ranch where people are actually working.

It only makes sense just as we wear our pants inside our rubber muck boots or even our leather work boots today when working in the mud or around livestock. Mud and manure wash off of boots easier than out of pants and cowboys of that time were wearing those same pants for weeks or months at a time. Plus thorns and sticker bushes don't snag leather boots like they do pants.

i think that's far too wide a generalization.  Most working cowboys I've known, maybe only a few hundred or so, in my 70+ years are of the "never run when you can walk, never walk when you can ride" mindset.  Stable work is for the youngsters, stable hands or tho7e that're still developing their saddle & rope skills.  Wearing pants inside or outside the boot is more a statement on style than practicality.  It's also driven by regional influences on style and personal taste.

Hmmm, my born in 1914 Montana Cowboy/Farmer father claimed only Roy Rogers and Texans stuffed their pants in their boots.  On the outside keep stuff from getting into the boots.  If mucking the muddy shitty stable pull pants up and stick on the notched top so they don't fall down and get dirty

Mighta also been your Dad's way of sayin' "drug store cowboy".  But hey! id I've get 10-11 rows of multi row stitchin' on my boot vamps, why not show it off? 

  Well OK 

I'll have to give the "nod" to Griff.  After all it be some apparent he be several days older-n-dirt.   

Although, we both have a preference for Revolvers that load from the FRONT and Brass Rifles that ALSO load from the FRONT 

I only have two ‘66 muskets and plan on letting them patina. I do however tumble and polish my brass as it makes them easier to find. Please don’t use sandpaper on your rifle.

Don’t shoot black powder but do have some black rifles…oops wrong shooting sport. When I want to win or be as competitive as possible I shoot my Marlin 1894 CL in 45colt, when I don’t care i shoot any of my other cas rifles. My go to sg is my M24 Marlin pump but I like my M30 20 ga too. For WB I run a M12 riot. Being the progressive club that we are my favorite handgun setup is a Smith or Colt DA in a crossdraw with a 1911 in a flap strongside [ala Rico Fardan] but a pair of DA Smiths, Colts or Webleys work too. My default is a pair of 4.5 inch Vaqueros. Whenever I do my Tim Strawn impression I carry my nickel 1911 and a birdshead Ruger as they match my silver nose.

MSM weather forecast say's heavy rain will end soon   
Well, perhaps someone there should look outside... It isn't even drizzling.
Light clouds, and nothing on the radar, except the western panhandle of Florida.
Perhaps that will reach mid-Fla. this evening 

Habitual weekly migration to my friends' LGS. 
 I still carry on that tradition my late shooting pard and I did for many years.
Nearly every Saturday, less we were at an NCOWs match or perhaps the gun show in Melbourne (Fl).