Making the Deliberate Choice to Stop Wearing Grody Pajamas

I’ve always been the kind of person who has strategized her clothing to get the most wear out of it. Even as a teenager, I would never wear new jeans and a new T-shirt on the same day; it would be new jeans with old T-shirt, or new shirt with worn-out khaki pants (it was the ’90s, we all had that dismal pair of Gap-inspired khakis).

When I started working, I never bothered getting “transition clothes” to fill the hours between getting home and going to bed; I’d come home and immediately put on pajamas, because I didn’t want to wear out my good Ann Taylor Loft shift dresses.

It was a personal triumph when I owned enough office clothes that I could go a full two weeks without repeating an outfit. That, to me, felt like the first step in “making it.” I gave those clothes the best care I could, and I have six-year-old Loft dresses still hanging in my closet today.

But I rarely wear them. Now, I work from home, which means my wardrobe looks something like this:

The “almost useless in fall and winter” is because I will inevitably push the “sundress plus cardigan” look until mid-October, although I know I shouldn’t. It never looks quite put together, even with the spaghetti straps hidden under the cardigan.

Here are some other things that I do, even though I know better:

— Wear hair pulled back in one of those skinny athletic headbands and a ponytail, instead of taking the 15 minutes to add product, blowdry, and style it.

— Wear ratty, pilled T-shirts because I’m afraid of wearing out the good T-shirts.

— Change into my ratty, pilled pajamas as soon as I’m done working.

I sympathize very much with Isabel Slone in her Hairpin essay about making deliberate outfit choices:

I have a tendency — and this is another poor kid thing — to reach for my crappiest clothes first, because I always imagine I’m “saving” my nicer clothes for imaginary occasions that never come. For Project 333, I picked out some of my favorite pieces, and the feeling of lounging around in a wicked Black Flag sweater instead of a pilling Michigan State sweater is indescribably luxurious.

There are probably a lot of us like that, who come home and put on old, crappy clothes — or who go through the day with some kind of secret worn-out item bolstering the rest of our outfit, whether it’s the sock with the hole in the bottom or the layering tank with a frayed shoulder seam that shouldn’t matter because it’s layered underneath something else, but still manages to rub against the skin.

I don’t believe that unfashionable people are by default invisible, but I have definitely gone outside wearing something old or something I don’t like, hoping I won’t see anyone I know and hoping nobody else will notice me.

And I don’t necessarily believe that our clothing determines our worth, or that clothing is related to creativity — I have written plenty of words while wearing clothing with holes — but I have always found this section of Julia Cameron’s The Artist’s Way to be Relevant to My Interests:

One of the clearist signals that something healthy is afoot is the impulse to weed out, sort through, and discard old clothes, papers, and belongings.

“I don’t need this anymore,” we say as we toss a low-self-worth shirt into the giveaway pile. “I’m sick of this broken-down dresser and its sixteen coats of paint,” as the dresser goes off to Goodwill.

By tossing out the old and unworkable, we make way for the new and suitable. A closet stuffed with ratty old clothes does not invite new ones. A house overflowing with odds and ends and tidbits you’ve held on to for someday has no space for the things that might truly enhance today.

But Slone’s “the feeling of lounging around in a wicked Black Flag sweater” stuck with me. My real pajamas are so old and grody that, when I stayed in the group Airbnb we put together for San Diego Comic Con, I wore fake pajamas. That is to say, I wore a T-shirt that would otherwise have been a daytime T-shirt, instead of the faded and torn “sleep tank” I usually wear.

Which is a long way of working myself around to “I read a Hairpin article and then bought a bunch of pajamas even though I don’t need them, because technically I could wear a sack to bed or whatever, but I wanted to feel like I was lounging around in something pretty and I don’t listen to Black Flag.”

And then I bought a bunch of other stuff too.

This cost me $130.35, or roughly $10.02 for each of the 13 pieces I took home with me. It still surprises me that it can be that simple. I can go to Old Navy and buy new pajamas and new leggings and fresh layering tanks and two dresses and a blouse with birds printed on it, and then I can come home and start throwing old clothes away.

(I can also “iron” those two dresses by wetting them down with water, smoothing the wrinkles out with my hands, and letting them drip dry on my shower curtain rod, since — unlike Amy Schumer — there is no space in my apartment for an ironing board. I may be in a position to be able to afford $130 in new clothes without saving up for it, but that doesn’t mean that the rest of my life doesn’t still have its pills and holes.)

After I finished throwing out everything that had a hole in it, I re-organized my closet and chest of drawers. Previously, everything was organized by category: shirts in one drawer, pants and leggings in another. ROY-G-BIV order, of course.

Now, I’ve got a drawer with the good T-shirts and blouses and leggings, and a lower drawer full of all the slightly worn out things. Some of them I kept for sentimental reasons, like the They Might Be Giants shirt I wore when I recorded my very first song, and some of them I kept because someday someone’s going to ask me to help them move, and I’ll need something to wear.

My goal? Every day that isn’t a “helping someone move” day, wear clothing out of the good drawer or wear one of the dresses I have hanging in the closet. Also, commit to wearing cute pajamas, instead of grody ones.

Most importantly: if it turns out I didn’t buy enough, I can buy more. It is okay to buy more. Old Navy gave me a coupon for $60 off my next purchase of $150, which means I could get 15 things for $110. I’ve already started making notes on what else I want to replace. (I have this old cardigan that smells like armpits…)

I’d like to go a full two weeks without taking anything out of that bottom drawer. It’ll feel, just a bit, like having made it.

Support The Billfold

The Billfold continues to exist thanks to support from our readers. Help us continue to do our work by making a monthly pledge on Patreon or a one-time-only contribution through PayPal.