That is my personal take on this issue too. Not saying boots with a suit can't be done - just that I can't bring myself to do it. I will, however, go with certain shell boots with most everything short of a suit (which I am doing today with gabardines, shirt, tie, and color 8 chukkas). Completely off topic - dress shirts - the BB luxury line slim fit is perhaps the best cut of RTW dress shirt on the market, IMO (slimmer than BB's other "slim fit" shirts, but not so slim a guy feels like he is in a wiener casing).
Hope Monday is treating everyone well ...
I find that the regular fit BB shirts are intended for larger body types, and that the slim fit is for people of healthy proportions . I'm a slim guy so I swim in the regular fit, and will only buy slim from now on. I have even thought of going extra-slim or whatever they call it.
If you think about it, it makes sense. Not like they have a cut called extra-wide, they just call it "regular".