One interesting note:
For about 7000 years, on the job footwear consisted of mid-calf to knee-high boots for men, who worked out of doors, either in farm fields or as soldiers, and sandals for women, who mostly worked indoors.
Some time in the last 200 years, women appropriated the tall boot as a fashion statement, and men were forced to rely on ankle-length laced boots. Today, women wear tall boots sometimes daily, with some women having enough pairs to go a week or more without wearing the same pair twice, but if a man wears tall boots, he either must be in some kind of costume, even if its a competition costume, say dressage, or gay and looking for some action. Men, it seems, are not allowed to wear the tall boots that used to define a man who worked hard out of doors.
My question is, how did this happen?
If you want to wear boots and still be considered an "I work hard out-of-doors" guy, cowboy boots should do the trick.
Of course, it depends on what kind of outdoor work you're referring to. Some guys wear tall rubber boots if the places they're working are particularly muddy, wet, or just plain icky.
As for women and boots... it could have something to do with the hemlines rising after WWI. As the hemlines got higher, it could be that higher boots were a way to preserve some sort of modesty so the women had more freedom of movement but still weren't technically showing "too much leg."
That's just a guess on my part, though.