Apologies for the log post... but I am in the same situation.
What I have now... these boots are amazing!! Comfortable (the maple calf leather lining is sooooo nice), great grip, durable, easy to put on and take off, velcro so no zipper to get damaged or cords to deal with, great protection.... they will sure outlive me!
Chippewa 12" Engineer Rugged Black Outdoor boots. Unfortunately, not water proof and no longer available...
So I have been looking for something that is waterproof and looks okay as well, and good to walk around, must be easy to get in and out of them without having to deal with laces... And that it will not break the bank. Not sure I want to go as high as what I have now... but do not want low boots either...
I have been looking at the TCX Hero WP... reading reviews now to see if I go with these or continue to look for something else... I really need them to be waterproof... These are but the reviews that I have read is that for the cold weather, on long rides, these tend to let some of the cold in... So not something I would be able to use on the long rides that I have planed for next year...
I have the itch for a Daytona boot... I have to say, man! they look great... Here is a photo of the Daytona AC Classics GTX Gore-Tex waterproof boots... But they look to be just a tad lower than the TCX... but they look amazing! And it ticks all the boxes except for the height... oh, and the fact that they are US$100.00 more than the TCX...
I do not want to ended up having to buy another one later one... so going back and forth between something that would look cool and be functional (like the two above), or just buy something that would work around the year like the Daytona Road Star GTX Boots ($$$$)... something that I could also use with my adventure bike in those 6,000+ miles trip that I do with friends :
So hopefully that helps you as well with some alternatives...
UPDATE: I ended up ordering the Daytona AC Classics GTX Gore-Tex waterproof boots in brown (got them from Revzilla...)