More often than not, I’m going to sleep in a pair of boxer-briefs and maybe a ragged old t-shirt. But when the mood strikes while lounging, I’ll forgo the sweatpants look (even if they’re nice sweatpants) for something a little more refined. I’m talking about, of course, a nice pair of pajamas.
Pajamas have a way of making one feel put together with minimal effort. Perhaps it’s the collared shirt or the old Hollywood glamor of it, but wearing a two-piece pajama set around the house feels very adult. Whether I’m in bed reading the New York Times or fucking up my Wordle streak, everything feels a little more grown-up when I’m in pajamas.
The key, as with most things in life, is buying the best quality men’s pajamas you can (and the five below are a good place to start). But it wasn’t always this way.
A Quick History of Pajamas
What people think of as pajamas today — any garment dedicated to sleeping or relaxation — is a product of industrialized weaving, religion, a widened middle class, and imperialism. In the Western world, from ancient times to around the 15th century, people would simply wear the clothes they wore during the day, turn well-worn garments into house clothes (therefore de facto pajamas), or sleep naked.
As textiles became more abundant and a larger middle class formed during industrialization, more single-function garments were introduced into the marketplace. This includes the nightshirt, or nightgown — the long garment that’s a bit like a dress with sleeves and a comfortable neckline — which was worn by anyone who could afford it, regardless of age and gender.
Britain’s invasion of India and the surrounding area eventually lead to the two-piece pajama set that we know today. The colonial expansion into the subcontinent introduced the English to the light and flowy garments worn by both sexes across India and the Middle East. They became a fashionable outfit worn throughout colonial Britain and eventually back on the island as well. The term pajama comes from Urdu, by way of Persian, meaning “garments for the legs.”
While the imperial history of the garment has long been overlooked, it’s interesting to think how we feel the ripples of colonialism reverberate in even the smallest ways today.
The Best Men’s Pajamas You Can Buy Today
While there is nothing wrong with wearing what’s most comfortable around the house, if you’re looking to update your loungewear game, these will give you a good night’s sleep and have you looking good while you do it.
Desmond and Dempsey Pocket Pyjama Set
Over the years, Desmond and Dempsey has undoubtedly cropped up on your Instagram feed. Its bold patterns and generous cuts make this a hit for anyone looking to lounge in something a little, dare we say, fancy. This set is my favorite, as it takes inspiration from workwear garments with added deep side pockets perfect for tucking a book in while you’re making your way from the bed to the couch on a Sunday.
Sleepy Jones Henry Pajama Set
Sleepy Jones is dedicated to crafting pajama sets that feel like an actual outfit and not just loungewear. The Henry has a more tailored shirt for a less boxy fit and comes in a variety of stripes, solids, and patterns. I’m partial to the Red & Cream Breton Stripe colorway, which gives some sophistication to the overall look. All that’s missing is a pair of loafers for an evening in with a Gin & Tonic.
Lahgo Washable Silk Short Set
If you run hot when you sleep, you may want to opt for a fabric that can keep you cool. Lahgo’s washable silk takes a notoriously finicky fabric and updates it for everyday use. With a generous cut short and tee, this is a loungewear set that easily keeps you comfortable and cool on even the hottest nights.
Piglet in Bed Gingham Linen Set
With its array of bedding options, it’s no wonder that Piglet in Bed would transition into the pajama game. This linen pajama set has a classic feel and generous cut, making it a great option if you’re new to the pajama game. And don’t trick yourself into thinking linen is just for summer. This is a great option to keep cool if silk isn’t your thing.
Tommy John Essential Pajama Set
If you’re not ready to go full-on into collar pj territory, I suggest going with this Tommy John set. Great for kicking it on the weekends, it comes with a loose fitting t-shirt and pajama pants. Made from micromodal, spandex, and supima cotton, you’re getting a buttery-soft fabric blend that’s breathable but still insulating for colder nights.
Emma Willis Cashmerello Pyjamas
For those who take their lounging seriously, this option from Emma Willis needs to be on your list. Emma Willis has been a shirtmaker since 1999, so the brand understands the male body and how to cut garments that don’t restrict. You can see this know-how at play in the loose, but still flattering, cut of the pajamas. The cashmere-Swiss cotton blend and mother of pearl buttons give one a real sense of luxury when wearing it.