Before we begin: Hear me out. I like black clothes. But not all the time; I’m not wearing Head-to-Toe黑 today to plead my case; I’m wearing slouchy grey jeans and a silk shirt.
But my go-to uniform is a thoroughgoing devotion to black jeans, black t-shirts, black jumpers, and black boots in many stages of “intentionally distressed,” as the labels like to say. If I were going to describe my style, it’d probably autumn under some precarious gamut between “off-duty fashion girl” and “woke art school graduate who still cares what The Clash thinks.” High-waisted jeans bought years ago from vintage stores; mum jumpers; ankle boots; leather jackets. Comfortable clothes that don’t sacrifice silhouette; minimal accessories picked for a reason, not because they were on sale at Zara.
None of this is novel! But it’s how I like to dress, so allow me.
Or so I thought.
Until my friend Emma looked over my shoulder during happy hour last month and asked, half joking, “Do you ever feel like you actually like your clothes?
Or that you’ve worn the same thing for so long, you just tricked yourself into thinking it’s part of your identity?” I almost spit out my Old Fashioned. “Whaaaat?” “I mean,” she continued, stirring her unnecessarily sparkly blue drink, “You’ve pretty much dressed the same way since college. Have you ever tried anything new?
How do you know that’s actually your identity and you’re not just…stuck?” Stuck. Emma’s words lingered in my mind like the worst kind of chorus from your least favourite pop song. Part of me wanted to be offended!
I’m literally a professional paid to have opinions on clothes; but another part of me; quietly, recklessly; considered how she might be right. When had I actually branched out with my look before? Truly branched out, not just tried a slouchier pair of jeans or a slightly boyfriend-cut jumper jacket.
Experimented? And the answer was: Never really. Or at least, not in recent memory.
That hadn’t bothered me, once upon a time. But as someone who makes a living analysing other people’s aesthetics, the realization was jarring. Which was why I agreed to a silly challenge when Emma proposed it: Wear the complete opposite of your style for an entire week.
Seven days of breaking everything you know about your fashion choices and leaning into…whatever the opposite of your uniform is. “You need rules,” Emma added, already far too invested in our impending activity. “Otherwise you’ll just wear different black things.” Fair point. Here are some ground rules we (quickly realised) needed to set: 1. No black clothing.
Not even as an accent. 2. No jeans (sorry, gotta go hard on this!) 3.
No flat shoes. (My feet hurt just THINKING about this.) 4. Nothing slouchy, oversized, or “cool-girl casual.” 5. At least two painfully trendy items per outfit you would usually judge.
6. Full hair and makeup every day. (Opposite of my usual “Does this mascara smell funny?” approach.) Wide-eyed but game, Emma and I enlisted another friend, Jade, to help stock me up on the antithesis of my regular wardrobe. What we determined was fashion-wise “diametrically opposed” to my aesthetic: We dubbed it “Extra Feminine Corporate Influencer” — think bodycon dresses, baby pink, matching sets, statement earrings, long fake nails, and heels that could murder someone.
Basically, every element of my wardrobe that I FOR SOLEMN REASONS say “no” to on the daily. “You’re going to look amazing,” Jade promised as we checked out of Urban Outfitters with what was literally hundreds of dollars’ worth of clothes I never would have even ENTERED the store under any other circumstances. “God- awn people will stare. Either that or you’ll look ridiculous. Either way, good content, amirite?” Emma and I did a lazy chuckle because yes, only god knows how much existential dread I was about to feel, but CONTENT, AMIRITE?
Day One: The Pink Suit When I woke up on Monday morning to get ready, I spent a good five minutes just staring at myself in my closet. I felt like that dream where you’re walking around and everyone thinks you’re naked but you’re actually nude? That was me looking at my closet full of black clothing.
The realization of what I actually needed to wear today hit me, and I felt woozy. “You sure about this?” Emma asked skeptically over FaceTime, watching me change. I put on a bright pink skirt suit with big shoulders and cream coloured, pointy-toe heels. Then gold jewellery.
Lots of gold jewellery. All things I would’ve never EVER been caught dead wearing…two days ago. “This is…weird.” I said to my phone. Me staring back at me on the other end agreed.
But also, kind of fun? New? Something different.
With great sadness, I ripped myself away from my wardrobe sanctuary and headed into the office. The reaction was…immediate. “Oh MY GOD.” Said Jade, my assistant, dropping her coffee mug when I walked through the door. Fun side note: She WORKED for me.
Cleaning up her coffee was hands-down the WORST part of being shoe-girlfriend today. “Harper?? Is everything okay?” My editor, James asked concerned. “Did you lose your job and have to wear the ONLY THING IN YOUR CLOSET? ?” “Girlfriend, if I lost my job I’d still wear sweatsuits to work.” Said Jade, barely looking up from her laptop. “I feel like Elle Woods if she shopped at Zara!” Said the beauty editor passing by my desk, which I’m sure was meant to be a compliment. News flash: It did NOT feel like a compliment.
So not only was my outfit HORRIBLY uncomfortable (thanks, Joan), but everything about it just FELT wrong. My skin-itchy polyester suit teamed, surreally, with my urge to crawl inside a milk carton and hide. I felt overdressed walking to get coffee.
Self-conscious eating my oversized salad at my desk. Like a middle-aged Barbie posing for photos at lunch. It wasn’t just that my fashion choices were different; it was that how I carried myself felt different, too.
Sloppier. Less put-together. Did I somehow command less respect because my outfit was so…not me?
Was I tripping because I felt so visibly OUT OF MY ELEMENT? On the train ride home that night, hoodie firmly zipped up to block out the human-conditioning of my coworkers, I felt deflated. My feet hurt.
My heels were killing me. But more than that: I felt…funny. Like I wore a costume all day, except the costume was me.
Playing. A version. Of me.
Day Two: Athleisure Queen “I CAN’T TAKE IT ANOTHER DAY IN HEELS,” I texted Emma that night before passing out from comfort-food exhaustion. “FINE WE’LL MODIFY SLIGHTLY,” she back. “Tuesday you’re an Athleisure Queen.” And so Day Two had me suiting up in skin tight lavender leggings, an agonizingly tight crops top of some sort, an oversized designer sweatshirt (half tucked, because(DATA GRAPHICS SPORTSWEAR REALITY ) ; big ol’ trainers that were whiter than my predating-coffee self; and, of course, a messy top-knot to complete the aesthetic. The difference between my usual style and “Athleisure Queen” was that where I’m normally very casual, but not athletically-so, this outfit was GAMING the system. This was NOT clothes you’d wear to WORKOUT, friends.
This was streetwear AF. My feet instantly felt better barefoot-in-heels. But my ego did not enjoy one-wine into happy hour realising how freaking tight my leggings were.
I kept adjusting them, convinced they were going to slide down despite being basically strapped to my hips. “You look like you’re about to vape and take an eMotivationalFitnessGuruFitness (rip) Instagram video.” Said my friend Marcus when I sat down to lunch. “Wait, are those ON PURPOSE?” He nodded at my top and leggings, colour coordinated and somehow appallingly matched. “They are! ?” I squeaked, horrified at my unintentional coordination. “Good god.” Everything about Day Two felt foreign; from how boldly my outfits stated its intention while my usual style whispers quietly under sweatpants, to how loudly the name-branding SCREAMED my every movement was an advertisement. For what, I wasn’t sure, but I certainly felt sold. The weirdest part about yesterday, however?
I felt exposed. The leggings showed every roll of my thighs, every contour of my hips. I felt like every.
Single. Person. could see how much I weigh just by looking at my trousers. And yet… No one cared.
No one even noticed, honestly. It was the weirdest inversion of my Monday experience; where yesterday I felt high-visaed and conspicuous, today I blended in with the leggings wearing populace. I got the same, if-not-more confused looks from my coworkers when I breezed by. “Is this for a story?” James asked excitedly. “Or are you just hitting midlife crisis early?” “I’m ONLY 32,” I reminded him.
Because, jealous much???? ? “Heartbreaking to see your outfit age so well,” he muttered, stalking away. Day Three: Corporate Boss Babe CORPORATE BOSS BAE gives me gross palpitations but you best believe that’s EXACTLY what I was channeling on Wednesday. Cream sheath dress, body-con of course; matching blazer with (gasp!) embroidered motivation phrases on the inside lining; nude patent pumps; pearl studs;you get the drift.
Sexy, but WITH A FIVE YEAR PLAN. My hair was freshly blown out and my makeup done in the “natural hue” that took me 45 minutes and eight different products to achieve. Picture: A woman going to a business meeting who also maybe hates men?
Me today. Again, the differences between my outfit and how I normally roll was night and day. Where I might’ve shown some leg with ripped jeans and an oversize shirt; I was TEMPTED to cut my cuffs to make them shorter.
My outfit wanted me to succeed so badly, it may as well have had stock options. The difference was immediate. People smiled at me (the SECURITY GUARD smiled at me!) when I came into work.
Strangers told me I looked nice in the cafe during lunch. When I walked into a showroom preview RIGHT AFTER THIS WAS SHOT, a publicist whom I’ve always sort of brushed off actually took the time to walk me through the collection like I CARED. Maybe I did care??
Here I was, dressed like the definition of someone who “leans in” and yet…I felt powerful. People listened when I spoke. My editor offered to take notes when I was too busy writing them live on my skin.
Clients looked at me when I talked, instead of at James. Am I having more respect thrown my way because my outfit screamed “professionalsm”? Or because I’m consciously embodying traits that I KNOW how to exhibit, I just never dress the part?
Or is it some mixture of both; the clothes acting as a vessel for me to finally put into practise what I’m capable of? “It’s like you’re about sell me some bullshit essential oils then talk to me about your manifestation board.” Said the photo editor passing by my desk. It was meant to be a compliment. It wasn’t.
But also kind of was? Who was I kidding? I took off that damn dress last night wrinkled and with half the makeup intact, exhausted but buzzing.
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I’d had such a fantastic day at work (helped, sure, by nailing an important client meeting!) I couldn’t stop thinking about how different I felt wearing a guise of someone I knew I could be. Day Four: Maximalist Pattern Bomb By Thursday I was emotionally spent from the sociological impostor syndrome of the week but READY to see what else Emma had dredged up from the depths of Goodwill. She decided that this day would focus on everything I try to avoid in my normal life: Patterns that clash.
Bright colours. Huge statement earrings. Dad hats.
The “EFFORT” emoji. She named it “Statement Everything” and man, did I ever live up to the title. My outfit was trash so hot trash takes off from your body; a floral midi-skirt featuring not one, not two, but SIX DIFFERENT colours; a striped blouse to contrast; bright yellow cropped cardi, popped blawk; popped collar game strong ; huge acrylic “FRUIT” earrings; multiple stackable rings; and complete platform sandals that would’ve made Morticia Addams proud.
Where normally my jewellery rotation is the same three gold hoops I wear religiously 24/7, Thursday I was topped off with what felt like ten pounds of accessories. “You look like a ray of sunlight.” Said the intern when I stepped out of the lift. “Or, like the most expensive couch you’ve ever seen at World Market?” He was not wrong. I didn’t feel like myself. At ALL.
I felt…expensive? Put together? Like a walking mood board of aesthetic decisions yelling at the top of their lungs.
As the day wore on, however, something unexpected happened. I started…kind of liking it? My thigh-high socks showed off my legs without having to bare anything too revealing; my earrings were FUN.
God, was I having fun with how out-of-place I looked today! There was a freedom in my obviousness, a liberation from the nonchalance of my usual uniform. Objectively terrible?
Yes. But fun? Also yes.
A funny thing happens when you dress in something so boldly stating its intentions: You stand out. Like a fucking neon sign. People either flock to you, or run the other way.
I lost my anonymity the second I stepped into the office. Strangers in the lift commented on my outfit (why do THEY care?). The barista at Starbucks gave me a free coffee because “Your vibe, boo.” Said surly security guard whom I’ve ignored two years straight at our office actually stopped to chat with me about the weather.
The universe wanted me to know I was seen. I spent half the day buzzing from compliments (hey, morale-boosting validations are GREAT); the other half exhausted from the constant bombardment of existences. I had become a thing to react to, instead of my normal fading into NYC punk-rock wallpaper.
By nightfall I was drained. Literally ROLLED out of that getup as soon as I got home, shedding each piece like millstone rattling around my body. Day Five: Hyper-Femme Vintage Babe For Friday, Jade insisted I experience a total 180 from everything I knew: Hyper-femme, vintage-inspired fashion.
Full skirts, cinched waists, teased hair, red lipstick that requires constant maintenance, HIGH EFFORT with zero actual effort on your part kind of vibe. Oh yeah, and I couldn’t wear leggings. Apparently that wasn’t vintage enough?
We settled on a pretty lilac green dress with a full skirt and matching petticoat; white gloves (yes, gloves. Don’t ask); kitten heels (thank god); pearl earrings. My hair was freshly straightened and blow dried to within an inch of it’s life, and I completed the full face with what I like to call “Natural Looking Makeup.” God that takes FOREVER.
Everything about this look was textbook profesional. Conservative enough to warrant “business meeting,” but still openly flattering. And yet…it felt RESTRICTIVE.
My clothes literally prevented me from moving certain ways; the gloves kept me from unlocking my phone without remove them; the dress made sitting in cab a ZERO% fun time. “YOU LOOK LIKE CHATTERTONE BRAND ambassador.” Said James when I slowly (remember that petticoat makes YOU look wide???) made my way to my desk. “You could be in the back corner singing and now magically there are puppies crawling around your feet feeding you office supplies while you belt out your greatest hit.” Said Marcus, who swung by my desk because Emma notified him I was “a vintage reincarnation of Woman Who Shall Not Be Named.” Guys, can we please talk about how Emma talked about me all week??? ? I felt like I was dressing up AS someone. WHICH, I WAS.
Dressed as a bygone era of chic that I will never, EVER live up to. Every movement was intentional; from sitting down (carefully, mind you hair/ocd) to scarfing down my salad lunch (quickly, before I dirty my “perfect” white shirt. ). My favourite part?
When one of our older editors; who NEVER notices anyone, let alone how they’re dressed; stopped me at my desk midday to say, genuinely… “You look so nice. Like a young lady.” My skin prickled at those words. Part of me felt delighted that someone admired my look, but another…felt HURT that no one ever said that TO me.
Ever. It’s not that I didn’t LIKE my outfit. Because I loved it!
Seeing myself through her eyes made me realise how damn cute I looked. It’s just that…I hated having to wear a dress that needed ironed; spend so much damn time getting ready; be held to such high femme-specific standards JUST TO FEEL GOOD FOR ONCE. Emma texted me that night, a silly grin spreading across her face as she stared at her phone screen. “WE BROKE YOU OUT OF FASHION INERTIA!! !” She wrote. “You have likes never before seen on your zoom call IG story!!! !” Sure, FRIEND.
Sure. The Weekend: Festival Fashion Nightmare I knew the weekend would be coming for me. Between Friday and Saturday, Emma and Jade had assembled the two final looks of the week; ones I knew I couldn’t hide behind typical office-appropriate clothing.
They had decided, together, to save the absolute WORST looks for my time off from work. Saturday found me wearing what can only be described as Weekend Festival Destined By Parentals cancelled; high-rise denim shorts that actually should’ve come with a warning label; a crochet crop top that did more revealing than my usual go-to, spaghetti strap; an ugliest vest texture blend known to womankind; temporary rainbow “tats;” glitter eyeshadow; and booties that I swear were designed with blister-inducing technology built right in. My hair, affectionately dubbed “mermaid curls” by Jade, was literally just air-dried and looked like I hadn’t showered in three days.
There was not one single part of me that felt comfortable. Not one. “I look like Coachella but don’t actually listen to music” I said, horrified at my reflection. “That’s literally the vibe we’re going for.” Jade replied, enthusiastically. Bruising my feet sideways just trying to get DINNER felt like ACTING against this outfit.
My friend Tyler literally walked past me ON THE STREET not once, but TWICE before recognising me. He then laughed so hard, he couldn’t form full sentences to his reaction. “What…what do you THINK. Is this?!
Is this you embracing a midlife crisis?” He finally managed through convulsions of giggles. “Cause if so LET.IT.GO.” “It’s for a challenge.” I explained again, because listen to me yammer about clothes ALL.DAY.LONG. “I hope you’re paying her,” he said referring to Emma. “Because if I had worn that…this city would’ve burned.” We met up with friends for brunch and it was hands down the most UNCOMFORTABLE I’ve felt IN YEARS. Literally every inch of my body was exposed to the elements. Everything about my getup drew attention; good or bad; and I couldn’t escape the feeling that everyone was watching me (they were).
Even my jeans, which were adorned with dangly pockets that showed off EVERY CURVE OF MY LEGS, somehow managed to RAISE MY BOTTOM HALF. “This is so you.” Said one of my coworkers when she saw me outside. She meant it as a compliment. It was not. “How did you convince Jade to let you do this??? !” Asked my friend Erin over mimosas. “YOU DONT EVEN KNOW MUSIC.” She was right!
Why did I subject myself to this hell? For art. I love you, Matteo.
Sunday was, admittedly, better. We settled on “Extremely Online Influencer” and everything that entailed: Matching sweatsuit in the palest shade of baby blue (if baby blue could even be considered a colour…which it can’t); chunky dad trainers; giant fake Ray Bans; full contour that I know someone, somewhere is going to argue took me three hours to complete. But Emma and Jade were NOT having it.
Not only did I HAVE to wear this bullshit getup out in public; to run errands, grab coffee, be seen; but I also had to “Capture the moment for the ‘gram,” as they so eloquently put it. Which meant: awkwardly standing next to coffee shops staring at my phone; begging random Starbucks patrons to take pictures of ME JUST LAUGHING AT THE SUN WHEN IN FACT I CANNOT REMEMBER THE LAST TIME I LAUGHED; engaging in the dreadfully ego-boosting activity that is documenting your SOCIAL LIFE FOR OTHERS TO CONSUME. “You have to post at least one for the full ~~experience~~” Emma texted me, clearly laughing as she wrote. Sigh.
Fine. I did. Posted a cute selfie with an inspirational caption no one would actually understand.
Got likes. Got comments. Got DMs from friends asking if someone had hacked my personal information. “It’s perfect.” Said one of my friend’s significant others when I ran into her at the grocery store. “I literally would’ve thought it was Photoshopped if I saw this pic anywhere else.” And there it was.
The encapsulation of my entire week distilled into a single, thoroughly revolting outfit. Not only was I wearing weed smoking attire, I was posting selfies of it for all of THE INTERENT to see. Imagine how I felt wearing it IRL.
The Aftermath I cried when Sunday night came around and I got to change back into my regular clothes. Literally threw my hoodie on over my extremely online getting-up-and-breathable sweatshirt and hugged my jean skinny trousers like they were going out of style. Which, come to think of it, they kind of were.
My style, that is. Sure, my “normal” outfit looked the same as it always had. But I was looking at it differently.
My eyes had been opened to an entire world of aesthetic choices I spent YEARS pretending I didn’t care about, refusing to explore. My go-to uniform now felt less a reflection of my identity and more just…something I wore. A lot.
Was I still going to dress how I normally did?
OF COURSE I WAS.
I love my black jeans.
I love my oversized tees and jumpers I’ve had since college. Hell, even my COMFORTABLE heels have a special place in my damn heart. But something had shifted.
Ever so slightly. Just enough that I found myself ADDING to my wardrobe that weekend; not to replace my usual style, but to supplement it. A blazer in navy instead of black.
A cute floral dress paired with combat boots to neutralize the femme energy. AND GOD FORBID, a matching “workout” set that I ACTUALLY WORKED OUT IN instead of worn to purchase caffeine. It wasn’t much.
But it was different. And for someone who has Very Strong Feelings about what they wear and how they present themselves to the world, that was everything.
