A quality pair of properly fitted/chosen pull-ons will fit the wearer's foot nice & snug after a little wearing. Trust me, I have sprinted after a buddy's escaped dog while wearing my western boots. No sloppy fit, there.
The uppers are supposed to have some clearance from your calf.
FWIW, I just bought a pair of Redwings today:
http://www.redwingshoe.com/productdetails.aspx?prodid=1162Black, steel toe, Redwing's comfy Supersole & Poron insole (just like my two pair of 6" lace-up steel-toe boots).
I already own a fine pair of western boots (rhino hide lowers, bull hide uppers), but I wanted something steadier when holding the kids like when we go to church. I don't want to take a spill on concrete steps with slick(er) soles and tall(er) heels.
All my Redwings are black and will take a polish, so I can wear them with everything from jeans to suits.