FASHION DARE: I Wore Whatever I Slept In To Work for a Week

Following the realization that I often repurpose sleepwear as daywear, I decided to take it to the extreme.
Publish date:
September 3, 2015
fashion dare, nightgowns, nightgowns as dresses, sleepwear

Sometimes I do this thing where I forget to change. True, the forgetting part is usually alcohol-induced. It’s an oversight.

To elaborate, because I realize that you’re enthralled by this article’s hook, me “forgetting to change” looks like this:

1. I wear an outfit to work, 2. I go out for drinks, 3. I go out for more drinks, 4. I come home, 5. I take off my shoes off, 6. I ideally but probably don’t brush my teeth, 7. I fall asleep, 8 . I wake up too late to re-plan what I am wearing, and9. I wear the same thing again.

This behavior was enough to prompt me to offhandedly remark via Twitter that I am something of an expert when it comes to repurposing daywear as nightwear and visa versa.

Please keep in mind that “nightwear” here does not in any way refer to the sexy tank top that I have kept tactfully hidden beneath my work-appropriate sweater, only to showcase in tandem with my third spicy cocktail at whatever New York bar is currently trending on one of the city’s ceaseless top 10 lists.

No, “nightwear” here is referring to full-on pajamas.

To the point: One Twitter follower responded that the specifics of this transitional manner of dressing should be the inspiration for my next post, and because I’m of the mindset that if one person says something aloud, 10,000 others must be thinking it silently (never mind the fact, of course, I have barely 800 Twitter followers), we are here together today.

To prove my point, I ambitiously decided to take on the task of wearing a piece of clothing that I had recently slept in (“a nightgown,” if you will) to work for five days. The individuals at my two different jobs were wildly impressed.

They didn’t tell me this directly; however, along with my inarguable skill for dressing like an ill grandmother, I’m also keenly aware of the perceptions of others. Sort of like how right now I can sense your extreme admiration for the maturity I obviously exude as a 25-year-old woman willing to undertake a potentially career-damaging move to prove an irrelevant point.

Before I begin, I’d like to thank the Olsen twins for making obnoxiously oversized and excessively billowing clothing “fashionable” for the masses. Otherwise, I’m assuming that I wouldn’t have a job right now.

Day 1

This here gem is a size 18 T-shirt dress that I ordered in bulk from Amazon to serve as a nightgown.

Styled with corduroy leggings (yes, I said corduroy leggings!) and black ankle booties, the nightshirt looks somewhat less like what it is and a bit more like what it could be if it were on a model and not me and I was not climbing a fire escape ladder in the hallway of my office building.

Consummate professional is my middle name(s).

This was, notably, my sleepwear of choice about 2 weeks ago. Since then, however, I have made a big switch that I’d like to delve a bit deeper into in “Day 2”’s example below.

Day 2

Back to black.

Or just, you know, “to black,” considering that I guess I started this post wearing white.

This day’s ensemble somehow felt a bit less “sleepwear” and a bit more styled. Sure — the fact that you couldn’t see the coffee stains dribbled down the front like you could on the white example above could perhaps have something to do with it, but I guess we’ll never know. (We know.)

You’ll notice that the trick to which I default in this particular occasion includes utilizing expensive high heels that I bought on a whim at a sample sale and to counteract the fact that I am essentially wearing a T-shirt without pants.

Currently my nightgown of choice, I can proudly say that I did, in fact, wear this beauty to bed the night before this lunchtime cafeteria photo was taken. Fun behind-the-scenes note: I also did not brush my hair.

Moral of the story: I can now confidently affirm that kale salads taste equally as unsatisfying while wearing a nightgown as they do while wearing daywear.

Day 3

Enter: the vintage front button-down nightgown, acquired from one of NYC’s best, Beacon’s Closet. True — some individuals may find the notion of acquiring another’s used bedwear appalling; however, I am no such individual. #Laundrydetergent!

This is one of my favorites, as the buttons lend it an air of authenticity while the long sleeves and exorbitant length allow me to, in essence, inhabit a cocoon while also working at an office.

Paired with steadfast black booties and a commanding phone voice, this nightgown has been catapulted into next-level status

Day 4

Time to introduce my second job to my odd sense of style. It’s all about confidence, here. Just so long as I don’t let on that I ate tortilla chips in bed last night in this third — yes third — oversized T-shirt from Amazon (buy in bulk!), they’ll assume it’s high fashion and leave me alone.

The strategy, as I’m sure you’ll be pleased to hear, worked splendidly. Again, by tactfully drawing the bulk of the attention to my choice of footwear rather than my apparel, I swiftly deflected the comments that might otherwise have been directed at my somewhat drab upper portion.

I did not, however (as can be gleaned from above photo) manage to manifest the poise that I’m certain would have assisted with pulling off this attire.

Day 5

Here we have an 3X t-shirt from Forever21. Officially not a meant to be worn without pants, in the interest of authenticity, I decided to wear this gorgeous number into work in the same manner that I would wear it to bed: pantless.

Dr. Martens top off the I’m-25-but-dress-like-I’m-15 look and showcase that if you try hard enough, you can actually make your sleepwear look less professional during the day than it did last night.

Again, to hammer the point home, I did not only wear this striped number to bed the night before, but the following night as well. Another fun behind the scenes note: I also did not brush my hair here.

Dear Friends: I hope that today you’ve learned a few good techniques for not only ensuring that you get the most out of your budget by (inappropriately) repurposing clothing, but that this same technique can help guarantee that you will never have to go on a terrible date again.

Dear New York City,

You have transformed me from a well-dressed style conscious individual into a woman too worn down to wear pants.

I don’t hate it.