The Montacute is a DRESS boot for a business casual office or the coffee shop, they are NOT a winter boot or a hiking boot.  That said, the beefy rubber outsole does provide good traction on slippery surfaces.

I wear a 10 1/2 medium with most leather shoes and boots but go down a half size to a 10 with Clark leather boots.  I put in an arch support and I wear them with thick socks and they are still roomy.

They were fairly comfortable around the house right out of the box.  After a few weeks wearing them around the house I wore them for a three mile walk around the neighborhood.  They were still a tad stiff but my feet were fine after the walk.  A few more long walks and they should be perfect.

The outer sole looks tough and shows no wear at this point.  The upper needs the same care as any good leather dress shoe, including polishing with a high quality shoe cream to keep the upper from drying out.