I own lots of Dr. Martens over the past 15 years but this is my first pair of heels. I really like them! They're comfortable from the start. I laced them up while zipped, and then tested the zipper a few times and they fit beautifully. I put them on and took the dog for a half hour walk and while my feet hurt a little bit, it wasn't near the usual doc marten break in process.
I should also mention that I don't wear heels. I own like, one pair, wear them once a year, and I always feel like a little kid clomping around in her mom's oversized high heels. I found these oddly easy to walk in, and extremely stable. No wobbly kid ankles in these!
My one issue is that they've got zero arch support. I suspect I'm going to buy some arch support insoles and put them in to see if it helps.
Overall, love them so far, and can't wait to wear them in! :)