What I Learned From a Week of Not Wearing Comfy Clothes

I wore comfy clothes.

My reasons for choosing to abstain from wearing comfy clothes at my desk were sound: Would dressing more professionally while working from my home reframe how I worked during my day? Would I be more seamlessly prepared for night events? Would I act in a different manner? Valid questions, right?

Living it out? Not so comfy.

Monday: I immediately regret this stupid plan — why not wear leggings all day if I can?! Isn’t that the dream?!? Leggings are pants, according to smart Americans, anyway! But I get up and immediately dress in the classic New Yorker’s go-to look of slim jeans, fitted black sweater, barest of makeup, and black sneakers. This works for the day, and I do feel a bit more office-y, but by 5 pm I look disheveled. I forgot how it feels to age in an office and not feel fresh by the end, and realize how lucky I am in my late-afternoon pre-evening-event showers. I have a work thing tonight. I change three times five times and so run a little late despite my morning prep. Ugh. But I look good.

Tuesday: I wake and immediately hurt. I’m not going to feel well today, I know; this is what happens in my chronically-ill body now when I go to events two nights in a row (even short, sweet ones, sigh). I decide to dress as if it was a radio show day and I was heading to Bushwick, with a play on comfy-clothes-meets-I-gave-a-shit: black leggings, knee socks, legwarmers (it’s cold and rainy out), a fitted shirt in a bright color, and a hippie long sweater. I put on makeup. I give a damn. I’d be fine if a cutie saw me on the street. When neighbors see me walking Mitra, I do feel more like my mid-thirty-something age, actually, even in the casual ensemble. But lesson:

  • Being comfortable has become a part of my M.O. for a reason; it feels better to be shrouded in soft, fitted material when my body aches. It feels better for unaching bodies, too! So, again, why the hell wouldn’t you wear comfortable clothes if you can!? Do men struggle with this? Is is just women’s clothes that are more restrictive? Hmm (insert chin-scratching emoji).

Wednesday: I’m up early to work. My usual routine is to grab my coffee and head straight to my desk. I love typing by 7 am, when the city streets outside my (now open!) window are yet empty. This morning is cold and rainy and gray, but deliciously quiet.

I attempt office-appropriate pants I’ve never quite gotten the hang of. I know I can make them cool and casual. I settle on a long cashmere sweater and sit to type.

By 7:45, I’ve changed again. The pants don’t work. They’re badass — deep blue, wide-ish legs, and they sit on my body right and feel stellar. But I don’t have the right top to match their shape and the cooly-casual office ensemble I’d feel right in. I slip back into my skinny jeans thinking of this Material World podcast episode reporting how skinny jeans are killing the fashion industry because of that very versatility. A white button down I forgot I had seals the deal. Lessons learned:

  • I should invest in cooler clothes. Like, clothes with more interesting textures and patterns. Most of my more formal clothes are one color and shapeless translation: boring — compared to my funkier casual clothes. As far as publically-impressive duds go, I need to clear out and restock.
  • I should buy more pants. I always need more pants. But now that I lost weight (No Sugar Challenge + sick winter) I have… three?… pairs of pants I like. I have to suck it up, head to the Turnover shop and buy, like, five I’ll adore and actually wear.
  • I should shower in the morning. I’ve switched to showering at night so that I can soak in a bath first and save morning energy for more important things, like work. But how put-together I feel in the morning is hit-or-miss. The miss part = grungy.

Thursday: In the shower by 7:30! I blow-dry my hair! I put on a long comfy dress, makeup, a bit of jewelry, shoes….

Walking Mitra, a tired Latino man smoking a cigarette in the tiny park by my subway, one work boot removed to sooth his already-aching feet, told me (in Spanish) that I am a very beautiful woman. I replied “thank you” (in English, because I understand and speak conversationally but am shy about slowly my brain speaks it nowadays), and as we walked home felt vindicated by the extra work. There is something to be said for having that part done early (though I missed my immediate draw to my desk and lost out on those first productive hours in the process.) A cousin comes over for dinner, and I feel like an adult, dammit!

There is something to be said for having this done early — a rule I used to impose upon myself regularly. But I also miss the precious, early-morning moments at my desk, when my body is groggy but my mind is clear, and words are the only thing that matter.

Friday: Skinny jeans, comfy top, makeup, done. Someone selling clean energy comes to the door (yay), and I’m not embarrassed to open it.

Saturday: I’m spending the day with an editor-friend in Queens, drinking tea and eating dosas and sharing some of my favorite hours of the every-four-months-we-coordinate-schedules. It’s hot out. I put on an old sleeveless jumper and pull a light sweater over it. I rewash my face, put on makeup, and realize my hair feels increasingly more annoying. Translation:

  • I should get a haircut. I have long hair, and usually just throw it up in a knot. But I now realize it’s breaking more from being so often tied, and if I get a trim it’ll be easier to leave down and — especially if I get some fortifying shampoo — look healthier.

Sunday: I’m allowed comfy clothes today. Even though Mitra gets me up too early, I put on a decent leggings-top-sweater outfit, a sheen of makeup, and clip my hair back before we go on our walk. I feel less grungy than I normally would and just as comfortable.


I’ve shied away from presenting myself with confidence.

This is not a new conundrum. Four years ago now (?), I worked with my life coach on this. I had started gaining weight (both from illness and lifestyle) and was overworking in my job. I had been dating a friend, it started feeling serious, we ended it, and I was confused by that all, feeling that much more unattractive and unsure. So much of life felt in flux. I didn’t know how I wanted to identify myself visually, and caring too much about how I looked outside when I knew I had work to do inside made me feel superficial.

She suggested I look at how I dress as an expression of myself. I’m a creative person, right? So how did I want to express my creativity with my appearance?

This helped then, but does even more so today. Thinking back on this week, and on how I’ve felt in my skin and in clothing overall, I feel most comfortable and confident when not wearing “business casual attire.” The reason why I couldn’t make those blue pants work was because the pain tops and button-downs I paired them with looked so plain on me. So The Office. Which is an excellent television show but not me. And even though I’m pondering and being open to working amongst other humans a few days a week, I can’t see myself in a too-corporate gig. And even if that happened, I don’t see myself conforming to fit that. I need to combine the style I’ve curated with my comfy clothes — where I have more patterns, colors, and different cuts to layer — with a more formal attire. Combined with the rest of this Year’s studies, I have a feeling that will mean investing in used clothes of better quality, that feel just a bit different than what I already have.

Excellent sense-of-self and social interaction study, here. Challenge 7.3 done.


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