I wear a regular width size 9 and have a "regular" heel.  I found the boots to be true to size.  The leather is stiff but I expected them to be.  I bought them in October and have only worn them about six to ten times and only two of those times were for all day.  I might still be in the breaking in phase.  They are made to last and I'm sure it will takes some time to "make them mine."  The front of the boot is fitting nicely and molding to my feet without any problem but I am having problem with the heel.  My heel slips and I get blisters.  I can't wear heavier socks or else the front would be too tight.  I can't use any kind of heel strips because they come loose when putting the boots on.  I'm puzzled about the heel fit. Maybe if the front loosens up a bit more then I can wear heavier socks.  I have other boots that are comparable in quality (not as stiff and rugged though) and they felt good right out of the box.  I'm new to this type of boot.  Frye has a great reputation and I love the look of the boot and the quality.  I'll update today's comment as time goes on.

April 2013:  Unfortunately, these boots are not getting better with time.  My heel still slips.  I tightened the straps hoping that this would keep my heels from slipping.  It didn't help - just made it hard to get the boots off or on.  This boot just doesn't fit well in the heel and rubs. I wish that I hadn't bought them - one can't wear boots if they don't feel good.  Good reason not to buy off of a website without knowing how they will fit. Other reviews say they feel great - this is the only brand I've ever bought (from a website or not) that felt so bad.