My Sloppy, Sad Adventure in ‘Pajama Dressing’

Photo: Getty Images, Imaxtree, Getty Images

Every Christmas my mother would buy my siblings and I a pair of pajamas as a present. I haven’t really grown since the sixth grade (even at my tallest, I was always still the shortest, a Peter Lorre–type figure in all photos), and as a result have a lot of pajamas that still fit — enough to suit all moods and all seasons. I have a lime green pair with cherries inexplicably printed all over the pants. I have a tiny pink teddy decorated with seventeenth-century scenes. I might actually have a more voluminous pajama wardrobe than I do a regular clothing wardrobe. New clothing is so hard to buy: You have to go to a store and try it on and then come to some sort of Socratic conclusion about it. Pajamas are less judgmental.

So when Marc Jacobs paraded pajamas down the runway at Louis Vuitton and Rihanna and Sofia Coppola showed up at parties in pajamas like tiny Julian Schnabels, I was elated. If pajamas were fair game to wear to actual events in the day, my wardrobe actually became much larger and significantly more cutting-edge (I usually hew to the more classic side of the spectrum, not so-called “runway trends.” These designer pajamas were so cool, like better-cut, ultrafeminine suits that a very short person could wear. One problem: I had not seen any people that were not Rihanna actually wear pajamas out of the house. Am I Rihanna? I cannot wear a sweatshirt that well! Am I Sofia Coppola? Not at all! My eyebrows are terrible. (Although one time I saw her having brunch at a place I failed to have brunch at). But you never know who you are until you try. And in that spirit, I will wear pajamas out of the house and see if I will become Sofia Coppola. Or, at least, enjoy brunch as much as her.

Day One, Brunch:

On this first day of the rest of my life, I decided to wear the pajamas my mother most recently bought me for Christmas. They consist of a chambray button-down pajama top and slightly cropped pants to the ankle. Both garments are light blue and piped all the way around with a darker blue border in a rather stiff uncomfortable chambray, like something someone in the middle of the Great Depression would wear to bed. I paired them with a dark blue cashmere cardigan and loafers, like I saw Sofia Coppola try. It is an interesting look. In some lights, it looks okay, like Björn Borg in an all-blue outfit. In other lights, I look like an unkempt nurse.

I decided to meet my friend at Prune for brunch. The wait was very long for a table and we passed the time by people watching. My friend, who I had warned about my pajamas experiment, was supportive. “It looks fine!” she said to me, in an encouraging way. I needed this help to my self-esteem. Everyone waiting outside of Prune is always very fashionable and wearing a massive fur coat and uncomfortable-looking shoes. I felt very comfortable in my pajamas but a little out of place. They were very roomy and lumpy, which is good if you are trying to kick someone while lying in bed with them, but not good if you are trying to look chic. I even put a tiny belt around the shirt, but that did not help at all. The pants were unexpectedly poorly tailored and top was like wearing a tent with sleeves that also had piping.

At Prune, no one gave me much attention, positive or negative. Definitely no one seemed to notice I was wearing pajamas. They just kept asking me if I wanted a Bloody Mary like nothing was happening before their very eyes. I even kept yawning, but it didn’t matter (I suppose they are not detectives). After brunch, my friend and I headed to J.Crew, to buy more pajamas. Although I have a LOT of pajamas, I needed a fancier pair as I was going to a birthday party that evening and the cherry pants were simply not going to cut it. I bought a pink pajama shirt printed with tiny flowers and piped in white. I also bought a belt to go over it to mimic actual tailoring. As I approached the counter to pay for my pajamas, one of the sales associates said, “Hey, are you wearing pajamas?” Finally, someone noticed! Sure, they noticed while I was actually buying pajamas, but I do not consider that a clue. The sales associate smiled at me and I took that as a polite cue to leave the store.

Day One, Party Time:

For this evening’s birthday soiree, I decided to wear the pink nightshirt with a belt over it, sheer black tights, and high heels, in homage to Marc Jacob’s Louis Vuitton runway looks this year. The pajama shirt, when belted, was rather short. I think I looked like a cabaret performer in Macau in the thirties.

“Hi guys! I’m wearing pajamas,” I said the minute I opened the doors of this birthday party.

“It doesn’t even look like pajamas that much!” said a person in response.

“Oh,” I said.

Later on in the evening, my stockings sprouted horrible runs and I kept trying to keep the shirt from riding up and exposing said runs. I went into the bathroom a lot and scrutinized my outfit. I felt a bit insecure. Although no one thought I was wearing pajamas, I knew, and it made me feel underdressed. Also, everyone else was wearing a dress like a normal person that lived in society. I made a pact never to hate on new clothing again. I even vowed to buy a Rihanna style sweatshirt.

Day Two, Brunch

Another day, another brunch! Honestly, what is Manhattan? Just a long episode of Sex and the City, apparently. I met my friend for brunch at this place called “Hu Kitchen.” (Hu, stands for Human. There is a lot of kale served there. I picked the destination, obviously.)

For today’s outing, I decided to wear a blue nightgown with a cardigan over it. Marc Jacobs also showed nightgowns this season (always with the cardigans! Why!) and so I would give this new style a try for variety’s sake. The nightgown is rather plain and unadorned but not, thankfully, at all see-through. It has tiny straps and looks a bit like the dress Lainey wears in She’s All That when she gets made over except much looser and a little more Mennonite. It is made of a very study polyester blend and was a gift from my mother. I hoped that it could pass as an actual dress. Sort of, except it was very baggy, like almost all sleepwear, I am realizing. I think you have to tailor pajamas. Especially if you want to wear them outside.

“Guess what,” I said, as I was eating something called a “cashew cream” (I don’t know). “I am wearing pajamas.”

“That doesn’t look like a nightgown,” said my friend.

“It is a nightgown,” I said, taking off my cardigan. “See!”  I exposed the nightgown’s tiny straps and awkwardly long hemline.

“I guess it does now,” said my friend, doubtfully.  “Do you really wear that to bed?”

Day Three, Fin.

Today, I decided to wear my blue-piped pajama shirt with jeans to lunch. This looks by far the most normal of any off my pajama-inspired looks, but I also hate it the most. Yes, it is the most socially acceptable, but I am already sick of all pajamalike things. It’s like a more precious version of a blouse. Chambray is a hard fabric to wear all the time. It was wrinkled from the wear of the weekend and seemed to attract dirt.

“I’m wearing pajamas, okay?” I said to my friend. We are eating tacos.

“Okay,” said my friend. He just ate his taco without comment. The experiment is over now, I decided. I am never wearing pajamas again. I am just wearing T-shirts to bed from now on. I am mad at pajamas.

In conclusion, pajamas are a hard, wily, and embarrassing thing. They are more like odd shapeless bags instead of clothing. Maybe if you buy really expensive pajamas they fit you like a glove, but I don’t even know if it’s worth it. No one seems to even understand the important style statement that you are making. One would think you would at least be validated by shock and awe when you defy convention. But no one cares that you are doing that. We live in a jaded society.