I’ve never understood traditional pajamas. Who wants to sleep in a button-down? What’s the collar for? Who wants a sexy nighty when Hanes white T-shirts exist? Nightgowns confound me especially. The idea of donning a large, oversize dress with the sole intent of climbing into bed strikes me as ludicrous. Doesn’t the material get caught between your legs? Doesn’t the skirt shimmy up around your waist?
And yet, the nightgown aesthetic in a general sense has always appealed to me. It elicits in my mind’s eye a kind old woman who’s a little sleepy, perhaps holding a candle, asking if I’d like some warm milk. (I do not, as a rule.) When I started to see nightgown-esque dresses on women on runways, Instagram and even Man Repeller, I was cautiously compelled for this very reason. (The mood, not the milk.) Whereas knee-to-mid-calf-length dresses remind me of those worn to church and under graduation robes, and full maxi-length dresses remind me of the beach, a true tea-length dress of the roomy variety strikes the perfect balance of casual and chic. It’s the ultimate uniform of the lady of leisure. It’s daytime nightgown alchemy.
I’m a little dress-hesitant though, generally, so I asked Harling to join me in taking this airy trend for a test-drive. Below are three days worth of nightgown-themed and inspired outfits, plus our thoughts on how we styled each one.
Day 1

On Haley: Caron Callahan dress, Saulidi sweater, Jil Sander brogues, MAC lipstick in Ruby WooOn Harling: Mes Demoiselles dress via MATCHESFASHION.com, La Ligne sweater, Trademark bag, Adam Selman x Le Specs sunglasses, MR by Man Repeller shoes
On Haley: Caron Callahan dress, Saulidi sweater, Jil Sander brogues, MAC lipstick in Ruby Woo
Haley: While this dress is not technically nightgown, it certainly engenders the nightgown “feel” in that it’s long and billowing and in a Peter Pan’s Wendy shade of light blue. I paired it with this knit cardigan to lean into the coziness the dress exudes. I felt wonderful in this, like I was both a shepherd and a sheep at once.
Harling: While styling myself for this story, I realized that the nightgown trend is perfect for transitional weather because when you’re wearing a literal nightgown but need it to not look so literal, the easiest solution is to pair it with a sweater or jacket. This first outfit was actually my favorite because it felt like something I would actually wear, maybe because the nightgown in question is covered by a gigantic sweater and therefore looks more like a dress or skirt. Regardless, it successfully combined my two favorite sartorial factors: fun (because I’m wearing a nightgown) and comfort (because I’m wearing a nightgown).
Day 2

On Harling: nightgown via Amazon, Mango coat, MR by Man Repeller shoes, vintage sunglasses, Zara earringsOn Haley: Creatures of Comfort dress, Topshop jacket, cowboy boots via Amazon, vintage scarf
On Harling: nightgown via Amazon, Mango coat, MR by Man Repeller shoes, vintage sunglasses, Zara earrings
Haley: Wearing cowboy boots with one of my looks felt inevitable. What’s a Western prairie look without a pointy boot? The camo followed easily, as I felt it hit on the same utilitarian energy of the shoes. Ditto for the scarf. I felt ready to milk a cow in this, which is to say: highly capable and also willing to offer you a glass of the warm stuff. All good things.
Harling: For this second outfit, I was wearing a true Little House on the Prairie-style, ankle-length nightie. I selected it from Amazon because of its name (The 1 for U 100% Cotton Nightgown) and its price ($39.99). Though I loved it from the get-go, I was wary of looking like a ghost and/or bride, which is why I piled on a red jacket, embroidered mules and cat-eye sunglasses. The resulting ensemble may or may not resemble something my mom might wear when she has to get up really early in the morning to walk our dogs and doesn’t feel like changing into real clothes yet, or it looks like pure genius. You tell me.
Day 3

On Haley: Sleeper dress, Marni pants, Adidas shoesOn Harling: Sleeper dress, Le Specs sunglasses, Céline boots
On Haley: Sleeper dress, Marni pants, Adidas shoes
Haley: I’ve wanted to pair sneakers with a nightgown since I saw this photo on Instagram, but as soon as I put them on, it didn’t feel quite right with the nightgown. It felt a little too “How ironic! A dress with sneakers!” So I fussed around with adding various jackets and eventually stumbled upon the idea of adding pants instead. It ultimately did the trick. I felt like a daisy-chain-making skater girl in this, which is to say, extremely cool. I think I’m firmly pro-nightgown trend, in all its variations.
Harling: This experiment confirmed my hunch that nightgowns or nightgown-like dresses are usually quite see-through. In terms of underwear, I think the move is to either wear black or white high-waist granny panties a la Carrie Bradshaw or skin-colored for a “Who me? Underwear?” effect. I accidentally opted for the latter in this case because I just so happened to put on my favorite beige briefs that morning. Kismet!
Haley and I have both been eyeing these Sleeper dresses-that-easily-moonlight-as-nightgowns for awhile though, and let me tell you, their teensy puff sleeves did not disappoint. I’m not sure if yellow boots were the right move in terms of footwear because they probably emphasized the whole “sleepy Annie Oakley” element. If I wore this again, I would probably pair it with lace-up gladiator sandals and big-ass rhinestone earrings — and yes, there will definitely be a next time. I’m behind this nightgowns-in-daylight lifestyle 100%. However, please answer me this existential question: Is a nightgown just a white caftan?
I’ll let you answer that.
Photos by Edith Young.