I always imagine redwings with that wedge rubber sole as the official workboots for the blue collar fashion style, I don't think enginer's boots as workboots, as I don't think anyone would climb up a ladder to roof top and walk around on narrow plank with cuban heels.Nowadays, every shoe is a work shoe in one way or another. For different kinds of work.
In the TFL context, I think we're talking about boots that used to be worn by the working class. A pair of shoes that were sturdy enough to do hard work in every day, but also looked passable enough to be worn formally on a Sunday.