Dear Homeward Bound,
It is starting to get colder out and I want to make my dog’s doghouse as cozy as possible. What can I do to make it a nice place for him when he wants to be outside?
Curious
Dear Curious,
Thanks for being concerned about keeping your dog warm and cozy … it’s only going to get colder.
There are several things you can do to make the doghouse a dry, warm space but most importantly, think about whether your dog is equipped to withstand cold. If he is a healthy, thick-coated dog in good body condition then he probably will enjoy time outdoors during the winter. But if he (or she) is older, suffering from any kind of illness or condition, has a hard time keeping weight on, or has a thin coat like a Boxer or a Greyhound, then a spot by the woodstove is probably a much better place for him to be.
Outdoor doghouses should be off the ground on posts or blocks to keep cold and moisture from seeping in. They should have an opening that is covered by a flap (think doggy door material) so that when they go in, they shut the wind out. They should be insulated inside and a nice way to do that is with straw.  Straw is hollow inside so it traps air and keeps the space warmer than hay or blankets, which can get matted down. 
Make sure to check them throughout the winter to make sure the outside stays in good shape and replace the bedding frequently.  
I hope you and your dog enjoy lots of quality outdoor time together this winter.
Homeward Bound