Our dogs have always been kenneled outside. We've tried virtually all the systems suggested over the decades. Admittedly, our dogs are getting (like their owners!) to be a bit 'high mileage', so it could be argued that we are over protective.
Here's what we do.....they all have a fleece coat to put on at the end of a long/wet day's work. All three go in the truck kennel, and typically, when we get home, they're toasty warm and largely dry. They do come into the house once they're dry and have some 'fire time', but, as someone else mentioned, when they've had enough they let us know and off they go. Outside they have draught free quarters (important!) and in their individual boxes they have vet fleece inside and a 'door curtain'. Their pallets in the run are a wood base frame, covered with StokBoard. The StokBoard is easily power washed, as is the vet fleece (or it goes in the coveralls washing machine!) This has worked for a lot of years now and we're confident that it protects our dogs well.