Very interesting topic. I would have to believe that, given the opportunity, they likely would have carried a knife that we today refer to as "tactical" or "modern". By "they" I mean both my grandfathers. Both were farmers and raisers of livestock. I didn't know my mother's father (Keith, my middle name), who died while I was still in diapers. My uncle still farms the land in Kansas that he did. I would guess that if Keith carried a pocket knife, it was inherited by my uncle. I should ask him what he carries. Besides farming, he's a real cowboy. He rides a horse and wrangles cattle for a living.
My father's father (Thom, also the name of my father and my brother) passed away just last year. I was fortunate to receive several of his pocket knives (inexpensive, but serviceable) after his death. He farmed the land and raised sheep. He was given an exemption for serving in WWII because as a farmer and sheep raiser, he was more valuable fighting the war at home (food and wool). Of the knives that I personally kept (the rest are with my parents), 3 are stockmans and 1 is a barlow. The story was that when he was hiring a new farm hand he would ask him for his pocket knife. If he didn't have one, my grandfather wouldn't hire him. If he had one, he'd try cutting a fingernail with one single motion. If it wasn't sharp enough, he still wouldn't hire him. He wouldn't trust a man who didn't carry a sharp pocket knife.
I don't think they would have carried something like a Sebenza, or even a Benchmade or higher end Spyderco. They certainly would have bought a quality knife, but wouldn't have spent a lot of money - no more than necessary anyway. Even so, it's certainly odd to think of such men carrying a knife like a Spyderco Endura SE or a Cold Steel American Lawman. As I said, given the opportunity, I think they would have. There's a reason 1-handed opening knives with pocket clips are so popular now, and popularity of traditional knives isn't what it used to be. But it just doesn't "fit". Any more than I'd expect them to rock out to Iron Maiden, put spinners on their tractors, or watch reality shows on TV. However, I think that's romanticizing it. I (we?) have a certain "image" of this generation in my mind, and an honest old stockman or barlow fits that image, not tacticals. But I think practicality on their part could definitely had led them to carry a Delica or Leek, had they the option. Even then, as farmers and raisers of livestock, a stockman certainly would be practical regardless of what decade it is.
It's an odd thing for me to think about, since the main reason I've developed interest in traditional knives is because of the connection I feel with that disappearing generation when carrying one, particularly following my grandpa Thom's death. Even though I think they definitely might have carried a modern knife, I don't like to think of of them doing so.
Not!
