The classic Timberland Euro Hiker is my all time favorite shoe.  I have a pair in the dark brown that I have worn for years and they still have a lot of wear left in them, but do look a bit roughed up so I am going to invest in a new pair this fall so I will have "nice" ones to wear out to town LOL.  The cheapest I have ever seen this classic leather style was about $130.00 dollars, but I have seen similar styles in other colors by Timberland for as little as $60.00 and have been tempted, but I just cannot bring myself to not stick to my favorites in color and material.  I can wear these shoes all day and walk forever and my feet never hurt nor do I get back pain ( a problem for me with my scoliosis), plus they support my ankles.  These are the shoes I will be wearing all the time when I retire in about 20 years (hopefully they will still make them or mine will still be around).  Defintely a causal shoe/boot that only goes with jeans or very casual khakis, but I have yet to meet anyone who has a pair who does not love them as much as I do.