I have my own pair of these in black and have worn Docs off and on for nearly 20 years.  I won't lie, they can be killer to break in but then they are the most comfortable shoes/boots I know.  This pair, however, was for my daughter and she absolutely loves them.  I bought her a box of extra large bandages and told her to use them on the backs of her ankles under her socks the first several times she wore them.  Luckily she did so she was able to break them in without much trouble.

They look great with all kinds of outfits from casual to even formal and have proven to be very durable.  It does take a bit of getting used to all the laces so if you want something you can slip on and off quickly, find something with a zipper.