How Aziraphale lasted 6000 years without pajamas, he’d never know. He didn’t enjoy sleeping, but he did enjoy relaxing, and he simply couldn’t lounge in his slacks and waistcoat.
The person who introduced him to pajamas was Crowley. Crowley, who loved to sleep and frankly, after 6000 years, had probably perfected the craft, owned the most luxurious silk pajamas. Aziraphale didn’t wear pajamas for the first time until that night they switched bodies. After being marveled and flustered all at the same time by Crowley’s naked body, he was taken aback by how amazing his skin felt under silk, and it wasn’t even his own skin!
After that night, Aziraphale invested in his own pair of pajamas, or what they really were: nightclothes. They were just the clothes he put on at night, to let his usual attire air out and to lounge and read more comfortably. They weren’t silk, like Crowley’s; he felt that was copying, and he never let anyone see him in them, either. He also got himself a bed, but never slept in it, just lounged. Half of the bed was taken up by stacks of books anyway.
When he and Crowley started being together, he wore them more often, in front of people. People, being Crowley and Eve. When he moved to the Cottage, he wore them even more. Especially since Eve practically lived in them if she could help it. Aziraphale was convinced she had made up “Pajama Days” just so she could spend the day in her pajamas and it is justifiable.
One day, Eve came home from a shopping trip grinning and holding a bag. She set it down on the coffee table in front of the sofa where Crowley and Aziraphale were sitting.
“What’s this, Eve?” Crowley asked.
“I got us all matching pajamas!” She said and pulled out the three pairs from the bag. They were orange and brown plaid flannel pants and a long-sleeve black t-shirt.
“No,” Crowley said. But at the same time, Aziraphale said, “Oh, how wonderful!” Crowley groaned, knowing he would have to wear them now, just to appease everyone.
Sure enough, that night they were all wearing matching pajamas and drinking hot cocoa. Of course, Crowley would never admit how soft the pajamas actually were, even if they weren’t silk, or how happy it made him see his Angel and Eve happy. Stupid pajamas.