Pajamas are the perfect work outfit
Think: Harold and the Purple Crayon, but make it fashion
By Jason Diamond / May 21, 2020 6:22 am

There are certain names that we associate with specific looks: Cary Grant is the god of suits, maybe only rivaled by Denzel Washington pulling off perfect fits for nearly four decades now. We equate Steve McQueen with a certain brand of grease-soaked ruggedness to such a degree that Barbour gave him his own posthumous collection. We will forever debate which James Bond actor wore a tux best, and the only person that has ever successfully pulled off a white shirt, jeans, cowboy boots and a sport coat from a Saville Row tailor is Fran Lebowitz. These are some of the gods of a specific style, and we must bow down to them. 

But nobody ever talks about pajamas. Specifically, nobody really notes how iconic James Stewart looks lounging around his Manhattan apartment and spying on his neighbors while wearing them in Rear Window. That’s all you see him in as he nurses his leg injury and tries to figure out whether or not the guy across the way killed his wife or not — and he looks cool as hell doing it. 

Grace Kelly was impressed with James Stewart’s pajamas. (Photo by Paramount Pictures/Sunset Boulevard/Corbis via Getty Images)
Corbis via Getty Images

Somewhere along the way we ditched classic sleepwear. I’m talking about the kind of outfit that Stewart wore, the type you’ve maybe seen your grandpa in. Not sleep shorts or a pair of sweats; pajamas. I don’t know why, but after rewatching Rear Window a few months back, I was ready to remedy that for myself. I ordered a pair of plaid cropped PJs from Brooks Brothers and began my new life as a pajama guy. 

The Brooks pair did me right. They didn’t wrinkle and became increasingly softer with each wash. But I wanted something more. I was looking for pajamas that I could lounge around the house in until I had to put on daytime clothes. For some reason, I was fine with wearing sleep clothes all day, but I wasn’t OK if that included a pair of shorts. So my quest continued, and along that quest, I amassed I nice little collection, a mix of new pairs of pajamas and vintage ones that I’d find on Etsy and other sites. My rule of thumb was if it could fit on into an advertisement in a midcentury issue of Playboy or Esquire, then I wanted it. 

Yesterday’s Playboy advertisements are today’s fit inspirations

The thing that I kept coming up against, however, was I don’t always love the feel of cotton when I was sleeping. I considered satin, but decided that brushes up against Tony Soprano territory. The perfect choice finally arrived in the form of a pair of grey linen PJs from Piglet. Linen! It feels great when you’re sleeping and even better to just bum around the house in. That was my first pair of 18-hour pajamas, a pair I could put on around 9 at night and wear well into the next morning or afternoon. 

My biggest takeaway from trying to wear a pair of PJs for as long as possible is you really have to have fun with it. While I’ve been changed thanks to the linen pair I have, I’ve noticed more people adding pop to their morning look. Aaron P. Levine tossed on some sunglasses and beads and made a whole damn look, while Gauthier Borsarello posted a sleep pullover that looks like a fun shirt for a giant. Would I wear that outside of the house? Absolutely. 

The point is that what you sleep in is just as important as what you wear during the day. My new rule is that if you wake up feeling like you look good, it’s going to impact the rest of your day. And these days, when we’re all cooped up feeling a little like Jimmy Stewart in Rear Window (hopefully sans the broken leg and murder taking place across the way), it helps when you can feel OK about lounging around in the same thing you woke up in.