I got that Hobes Wooly Hobe as a Christmas gift from a stylish friend, and you have hardly left my feet on weekends. My favorite thing at Wooly Hobe is because they are so warm and cozy (plenty filled with super soft lambswool), you don't have to wear socks even on the coldest winter days. Since I am a reluctant sock wearer (the ratio of sock length to shoe is far too important to me), it is a real gift not to have to decide which socks to wear.
The Wooly Hobe felt immediately at ease and did not require a break-in period. The only limitation I would put out is that they don't have much arch support or padding. So I wouldn't recommend them to people who need insoles in their shoes.
Also note the suggestion of the hobes for sizing: order a full size larger (or size up to the next full size).
For those looking for wool-lined (or sherpa-lined) shoes, here are a few more options to consider:
I am going to write a FIFW article for Wooly Hobe text me with styling suggestions!