How is leather easier to clean than denim? Just put the damn jeans in the washing machine. Hose them off outside first if needed. And no, cuffs on men look really ghey. A co-worker in his 40's wears 5" cuffs and Vans ... and he has a handlebar mustache. Yes, everyone is on high alert.

I keep my pants pulled down over my boots. If i don’t i get stickers and stuff in my boots.

I meant as far as staining goes.
I've got several pairs of wranglers that have mud stains around the bottoms. Which I don't mind.
It's just easier to scrape the mud off the leather and be done with it and not have to put another pair of pants on because they're in the washer.
Just a preference.

Working in the cattle yard, tuck inside of pant leg in boots.
Also slit inside of pant leg a bit, boot slides off easier.
Ever get thrown from horse, & boot get hung up in dtirrip.

If you wear Wranglers or cowboy cut/boot cut jeans instead of skinny jeans wouldn't have to slit them.

It’s not the only slit he has so he’s ok with it.

Maybe the guy bought his pants to fit regular shoe wearing and then wore them with boots. Buy your pants a little long for boot wear, that way when you sit down, your pants won't ride up over your boots...on the other hand, I once heard an old cowboy say, "If we weren't all different, we'd be just alike."