These boots are comfortable from day one.  I had another pair of Timberland Pro boots I purchased in 2004 and wanted an exact replacement.  That style was no longer available and these appeared to be the closest match.  The sole is taller and different on this pair - waffle stomper soles like to pick up 1/4 minus gravel and cherry pits left by the birds.  The leather almost has a synthetic feel to it - I know it isn't but it just has a strange quality.  The boots tend to have a wider than usual footbed - I like having room for my foot to move in my boot.  If you have a normal size foot for your shoe size and like a snug boot, these might not be the ones for you.  I got a great price on Amazon and wear these boots every day in comfort.

November 25, 2012 update:  The sole is kind of falling apart -- from the edges.  I wish I could have bought the old boots.

February 5, 2013 update:  sole continues to chunk off.  I can't recommend these boots.