In reply to goldmember:
Our dog live in a kennel outside for 16 years when I was a kid. The salient points of the design were:
Wooden, as an insulator. Heavy, felted pitched roof.
Off the ground - not damp
Entrance a snug fit to keep out draughts, and offset on the short side (ie not central) It meant that he could curl up and look out, or tuck himself into the corner.
Overall size not too big - room to move and shift, but snug and cosy
Filled with straw, regularly changed and topped up
Placed in a sheltered location, protected from the wind (i.e rain and snow couldn't blow in)
On really cold nights, you could see that he had closed the door off with the extra straw he'd been given.
It was always his place and he always seemed happy in it.
On the plus side, the house was in an isolated location and had trouble with burglars. Once the kennel arrived, within sight of the front gate , with a chain looping inside, that all stopped. 30-odd years after the dog passed on, the kennel is still there.