I Dressed Like My Mom in the 90s for a Week and Everyone Was Obsessed

It began on a rainy Sunday afternoon with an ancient photo album. I had returned home to Connecticut for the weekend to “help” my parents clean out their basement. In reality, I was there so I could eat from my mum’s pantry and do laundry for free like the successful adult that I am.

Between labelling Christmas bins and fighting over whether or not anyone would ever wear that bread maker again, I happened upon a plastic tub filled with dusty photo albums I hadn’t seen in decades. And there she was: my mum in all of her 19-naught-y glory. Photo after photo of her rocking outfits that could have come straight off of runway lookbooks today.

High-waisted Levi’s with the perfect taper. Oversized blazers and broad shoulders.

Slip dresses worn over tissue-box turtlenecks.

An entire rainbow collection of statement earrings that would make Etsy indie sellers cry with jealousy.

Doc Martens with floral skirts. Cat-eye sunglasses so small they might as well have been for cats.

Scrunchies. Tucked button-up cardigans. The whole nine. “Mum,” I said, flipping to a particularly solid page of her circa autumn 1994 self wearing a chocolate brown blazer over a vintage-y slip dress with cuffed ankle jeans and black leather loafers, “you were cool.” She rolled her eyes and swatted my hand away as she closed the album. “Those are just old clothes, Harper.” Except they were more than just old clothes.

To me, her closet was a time capsule; evidence that my mother, who is now almost exclusively seen wearing leggings and Target shirt dresses with garden clogs, had actually been stylish AF in her youth. That woman who asked me last week if “people still wear jeans” actually knew how to pull off 90s clothes better than almost anyone I knew. INCLUDING ME.

It was then that an idea popped into my head. What if… what if I dressed exactly like Mum for an entire week? Not as some sort of costume or grotesque vintage caricature of her earlier self, but as a legitimate styling challenge.

After all, fashion trends are cyclical. EVERYTHING 90s is making a comeback right now; slip dresses, square-toed boots, tiny purses that can hold approximately one tube of lip balm and half your credit card. I pitched the idea to Katherine, our EIC.

Fully expecting her to tell me to kill myself. Instead she considered, pens tapping thoughtfully against her desk. “Interesting angle. Family photo albums as styling inspiration.

But you need something more. Something punchier.” She leaned back in her chair, crossing her arms. “What if you recreated specific outfits? Pull photos and match the clothing as close to the actual photo as possible?” Within twenty-four hours, “I Dressed Like My Mum for a Week” went from a vague idea floating around in my brain to a locked-in article with an allotted photography budget and a strict deadline.

All I needed was approval from the one person who could make it happen; my mother, along with access to her ancient wardrobe. Thankfully, my mum is borderline-Hoarders when it comes to clothes and I was certain that even if she no longer wore them, the entire contents of her 90s closet still lived on in some storage bin at my parents’ house. “She’s going to hate me for this,” I muttered under my breath when I called to explain the concept. My mother did not approve of my idea.

At first. “Harper, no,” she said when I told her about the project. “That’s stupid. You shouldn’t do that.” “Why not?” I said, genuinely offended.

“It’s not stupid. It’s flattering, even. You rocked the 90s, Mum.” “Oh please,” she groaned.

“No one’s going to want to see that old crap.” She paused, and I could practically hear her reading through old inventory in her mind. “Plus, I wore those things. Like, wore them.

They’re worn out and gross, remember?” “I love worn out and gross,” I deadpanned. “That’s literally my aesthetic.” “It’s not,” she cut me off. “And what’s more, that was decades ago. When I had time to think about things like fashion. Now I’m just busy keeping your father alive.” “…Okay, revenge points.” I was silent as she continued to rant about how I would never find anything that wasn’t moth-eaten and covered in mildew at the bottom of her closet. “Fine,” I relented when it became clear my mother was not going to be an ally in this. “If you don’t want me to do this, I won’t.” But then I had an idea. “Is there any chance you’d wear them again if I bought you some new stuff?

Like, would you want to still look like a cool 90s mum or are you cool with dressing like us old folks now?” She loved dressing me and my sister for as long as we’d let her, so playing into her DIY stylist ego was exactly how I convinced her to let me rummage through her closet. “Absolutely not,” she said when I called her Sunday to confirm we were still on for Monday. “You want to do this stupid project, go dig through my closet yourself.” “You’re not helping yourself with that attitude,” I sighed. “Look, let me just come over and help you clean out the garage if you promise you’ll help me look for clothes.” It worked. Spending all of Saturday up to her hips in ancient photos was enough to give her version of nostalgia goggles and we scheduled a Sunday come-hunt-with-me carpal-tunnel-inducing extravaganza. She was right, Mum was right: All of it was there.

Buried under dusty bins of Christmas decorations andHoliday table clothes were her blazers. Her slip dresses. Those vintage Levi’s she swore died with us but actually fit me.

Even the Docs, still sturdy enough to wear despite being older than all of my interns. Some were banished to “painting/roof replacement clothes,” some were carefully wrapped in tissue paper and placed in labelled storage bins, but some; the lucky ones; were proudly displayed in her closet still, as if pulled from an old Sears catalogue. “I couldn’t part with these,” she said, holding up a sleeveless black slip dress with delicate lace trimming. “Your father bought them for our first anniversary.” She slid it up and down her body thoughtfully. “But I doubt it would even fit me now.” Hours were spent digging through closet bins and old albums, me squealing with excitement at each discovery while she grew more and more enthusiastic about the project, clearly enjoying showing off her old digs.

The burgundy blazer she wore to interview for her first “big girl” job. The vintage kimono-style jacket she found at a tiny flea market in Chicago. The oversized button-up shirt stolen from my dad’s closet that she swore was actually hers.

Come Sunday evening, I had seven full outfits curated and planned for each day of the week. Some we were able to source directly from Mum’s existing wardrobe; others were close enough substitutes that I’d be able to find from my own closet or vintage shopping around the city. Mum agreed to let me borrow her collection of chunky silver jewellery, most of which hadn’t seen the light of day since I was in middle school. “Just make sure you don’t lose this,” she scolded when I was packing up the jewellery box. “The turquoise ring was your grandmother’s.” Isobel grandmother was a bohemian flower-child with great taste.

If she was still alive I would’ve sold her soul to borrow these outfits for longer than a week. Getting the turquoise ring backstory from Mum was like inheriting the clouded buppie pieces early. DAY 1: MONDAY – The Boss Blazer Our week officially started with one of Mum’s most iconic looks, circa Autumn of 1992: an oversized charcoal grey blazer, her trusty black bike shorts underneath, slim-fit jeans cuffed at the ankle, and black leather ankle boots.

The photo featured her leaned casually against a brick wall, tiny silver hoop earrings dangling, hair pulled back into a low ponytail held down by……… wait for it….. AN ACTUAL PENCIL. Accessories included a thin gold watch and small cat-eye sunglasses.

Luckily for me, every 90s woman and her mother owns an oversized blazer these days so that was easy to handle. The jeans were liberated straight from Mum’s closet; vintage Levi 501’s that miraculously fit me and have me questioning every SINGLE modern jean I own. As for the pencil in her hair, well… let’s just say I wasn’t going full “au-curate” and stuck with a classic black Blackwing for accuracy’s sake.

When I stepped into the office Monday morning I felt like a boss. Literally wore-the-hell-out-of-this-blazer boss. The blazer itself had wide shoulders that made me stand up straighter.

The jeans werebroken in just so; no matter how hard I search thrifting through vintage jeans, that worn-in-but-not-really vibe still eludes me. And my god, the jewellery. All of my jewellery is practically tiny pixie dust compared to these feel-on-your-face silver hoops and my new favourite watch. “So, new outfit?” Simone, our fashion director asked as she took her seat at Monday’s morning meeting. “Sort of.” I replied, pulling out my phone to show her the picture of Mum I had taken for inspiration. “I’m dressing like my mum for a week.

This, is her from 1992.” She studied me for a minute, flipping through the pages of photos on my phone. “Blouse and jacket proportions are incredible. Very Helmut Lang/Denis costume but, I dig it.” If anyone other than my other editor was handing out gold stars, Simone was giving them out today. By lunchtime I had three people come up to me to comment on the blazer, and one intern had googled the brand of jeans I was wearing to see if she could get an exact match. “Where’d you get those?” she asked excitedly when I told her they were my mum’s actual jeans from the 90s. “I mean,” I replied modestly, basking in her envy. “Yeah, they’re from the 90s.” The absolute pinnacle of insanity came when I was picking up coffee to-go from the corner deli later that afternoon.

The guy working; who shall remain nameless but who also happens to have great style and serves roughly 85% of the fashion industry from his tiny corner coffee station- artfully swirled the cocoa mix into my grande latté and did….you guys. A DOUBLE TAKE. “That outfit is FIRE,” he said excitedly as he slid my coffee across the counter. “You’re going full 90s babe, but like, in the best way.” Had he but known how 90s it ACTUALLY was. DAY 2: TUESDAY – Slip Dress + Tee, BASIC AF.

Tuesday was inspired by a photo of Mum from March of 1994. A black silk slip dress worn over a simple white crewneck tee, completed with mum’s trusty loafers and chunky black ankle socks. All of the parents watched Melrose Place?

We dressed like them. Literally. The slip dress came straight from mum’s closet; that aforementioned anniversary gift from my father she swore she’d never got rid of.

It was a tad large in the bust and laughably short, falling mid-thigh instead of the midi-skirt length we seem obsessed with today. The tee was easy to style; I grabbed a vintage Calvin Klein I own that still lives in my drawers. Tiny backpacks proved to be impossible to find at my height so I subbed a small crossbody that evoked a similar aesthetic.

Slipping into this dress felt both nostalgic and revoluational. I’ve worn countless versions of this exact silhouette throughout my career but something about the proportions, ripped straight from 1994, felt revolutionary. The slight oversize of the tee under the tightness of the slip dress created a tension that I can’t quite put into words but feels very… nostalgic?

Katherine popped into my office Tuesday morning to drop off a stack of paperwork. “Where’d you get that shirt?” She asked, gesturing to my basic tee. “The shirt?” I replied, confused. “Oh. Uh, Mum owns a shirt just like it.” “You do realise that is an exact copy of something I just sent to Edit for that street style shoot last week, right?” She held up her iPhone, already scrolling through photos. “Yep.” I deadpanned. She showed me the photo.

An influencer wearing the exact same silk slip dress, same tiny backpack, down to the loafers. “This is wild,” Katherine murmured, still scrolling through photos on her phone. “She’s literally… copied?” “She is Boss,” I corrected. “Lemme show you another.” We spent the next twenty minutes pouring over photos of Mum’s outfits from the early 90s. Katherine marveled at how many current street styles were pulled directly from outfits she owned twenty…THIRTY YEARS ago. She sent me a Follow thread by the end of our chat so that, should this whole thing actually blow up, Mum is ready for her inevitable designer contacts.

Your grandma was literally stealing outfits from the future. Day 3: WEDNESDAY – Canadian Tuxedo, but make it Mum. By Wednesday I was fully in it.

I decided to take things a step further with Mum’s full-denim glamour look from summer of 1995. Photo features mum rocking high waisted, blonde-distressed light-wash jeans with an identically-coloured denim jacket, black quarter sleeve turtleneck underneath, and what I can only assume were burgundy ankle boots. Mum had her hair up in a low bun with wild pieces of hair framing her face, and wore tiny hoop earrings along with that stunning statement belt she still owns (Thanks for the loan, Mum! ).

The Canadian tuxedo isn’t new or revolutionary in 2025, but something about my Mum wearing that exact combo looked particularly fresh to me. The high rise of the jeans. The slightly cropped fit of the denim jacket.

How perfectly worn in the denim appeared, despite now being so spot-on with trends we ironically “recreated” it would’ve passed for authentic in the 90s. I pulled the jeans and jacket directly from Mum’s closet; thankfully we were still close enough in size that they fit! She actually picked out this entire ensemble from a Sears catalogue, y’all.

SHE BOUGHT THESE THINGS FROM SEARS. “This isn’t going to work for the office…” I grumbled to myself when I first got dressed, noting the sheer amount of denim I’d be wearing on a day full of meetings with two of our biggest advertisers. But you gotta commit to the outfit, am I right? Like every other day this week, I supplemented the look with items I already owned; the black turtleneck (similar), burgundy ankle boots (also similar) and replicated her messy bun hairstyle as best I could.

I even found the statement belt; a vintage silver piece with an oversized centre buckle, at the bottom of her jewellery drawer. The first meeting of the day went shockingly well. Our client; a beauty company looking to collaborate on sponsored content – actually commented on my “refreshing style.” The next meeting; with an older gentleman representing a luxury watch brand, was less successful.

No one could have prepared me for the afternoon coffee run. Tyler. Good lord, Tyler.

Boss editor over at some hip other magazine and the human incarnation of back-handed compliments decided to do a full-on double take when he spotted me walking back to the office. “Harper,” he said, eyeing me up and down like a cheetah sizing up a gazelle. “Bold.” Bold it was. I braced myself for some level of ridicule but he continued, begrudgingly impressed. “Seen this DIY drip all over Paris lately. Workwear denim is EVERYWHERE.

Consider yourself ahead of the game for once.” And with those words, he turned and walked away, leaving behind the biggest compliment I could’ve asked for that day; “It looks good on you.” Sidebar: Three separate Instagram users DM’d me Wednesday asking where I got my denim set. Our social intern even took a ‘fit pic’ of me in the outfit to feature on our weekly office style round-up. Kurt Cobain is spinning in his grave.

Or laughing. Either one would honestly be amazing right now. DAY 4: THURSDAY – Floral Babe with Fighting Boots.

Day four’s outfit was perhaps the most 90s of them all: a midi-length floral dress with spaghetti straps, tied over a white tee, completed with combat boots and an oversized flannel tied at the waist. Mum was standing in front of a local record store in the photo, baby sis in tow, rocking that perfect blend of feminine & grungy that every 90s mum dreamed of achieving. This entire look was nearly impossible to source exactly.

The dress is long gone, apparently a victim to a large paint spill Mum had while renovating her kitchen (?). We did however score a similar vintage floral midi at a thrift store near their house. The combat boots were straight from Mum’s wardrobe; still in unbelievably good condition considering how many years they’ve lived in her closet.

The flannel? Swiped from my father’s slacks collection. Guys, some things will never change.

Including his refusal to move on from the same five flannel shirts he’s worn for the past 30+ years. Walking to the subway that morning I felt like a punk rock version of Mrs. Claus.

The juxtaposition of flowy dress with heavy boots created a silhouette that was at once sweet and dangerously aggressive. The flannel around my waste was purely for show, seeing as we’re well into April and I refuse to wear a heavy jumper to work… but it needed to be there. Visually.

If day three was any indication, this look was going to turn some heads. And it did. Not all of them were welcome.

Our downstairs neighbour; an older woman who enjoys commenting on my “unique” clothing choices as I’m dropping off my laundry in the lift, actually stopped me in the hallway to give me her concern. “Are you in a play?” She asked, eyebrows raised in worry. I opted to forget day three happened and power through Thursday with my mum-inspired floral power fantasy. Reactions at the office were overwhelmingly better.

So good, in fact, that Emma from Beauty Department stopped me in the hallway to ask where I found that perfect midi dress. “Classic 90s,” she replied when I showed her the original photo. “Betty from岁月留声曲?” Emma and I spent a good twenty minutes comparing outfit notes, swooning over how incredibly “ahead of her time” Mum was in this specific photo. And then Emma said something that stopped me dead in my tracks; “I feel like I’ve seen you wear something like that before…” Day four was also the day I got catcalled by our parking lot doorman. Yes, harassed for how I was dressed WHILE AT WORK.

Mother of dragons if this isn’t the reason I decided to look 50% like my mum from 25 years ago… All jokes aside, Thursday was an absolute SMASH. By mid-afternoon I had been sent two Instagram DMs from readers asking where I found the denim set, one of our assistants had snapped a fit-pic for the office newsletter, and people were actually stopping me in the hallway to compliment the outfit. If mum could see her wardrobe positively FLOWNING my stylist career right now, I would die and resurrect as a fashion icon.

DAY 5: FRIDAY – Mum’s Uniform Outfit number five was what my mother referred to as her “mum uniform” circa autumn 1997: leggings and an oversized cardigan, black ankle boots, and a white tee. Simple. Easy.

And yet, there was something about how mum styled this particular ensemble that I couldn’t WAIT to try. She was pictured standing in our childhood kitchen, rolling up her sleeves to reveal cream-coloured cuffs and pushing her hair up into an effortlessly chic low ponytail. Paired with small hoop earrings and what I can only imagine was her everyday makeup routine; neutral eyeshadow, cream blush, lip balm.

Mum was basically wearing what we argued was a “basic bitch” uniform twenty-five years ago. Items for this outfit were perhaps the easiest to procure. Everything but the leggings I already owned; similar enough to the original pieces that reading photos side-by-side you’d be hard pressed to tell they weren’t the same items.

The leggings were borrowed from Mum’s drawer; rolled at the bottom to perfectly mimic the cropped appearance in the original photo. Walking into work that Friday morning I was fully expecting this outfit to blend in. Current athleisure trends have been VERY similar to Mum’s generic mummy uniform and I feared her Friday look would be lost on the stylish metropolitan extras of NYC.

It was anything but. “This one is different,” Katherine said thoughtfully as she sipped her morning coffee, stopping by my desk to walk me through the weekly newsletter edits. “It’s simple, but I love the proportions.” Simple. But perfect proportions. Say that ten times fast.

My theory was confirmed when lunch rolled around and I found myself seated at a table full of women who worked in various departments but all leaned heavily into their personal style. Our newest coordinator; a recent graduate who knows way more about aesthetics than I’ll ever know- paused as she studied me from across the table. “It’s like normcore but intentional. Mum-core?” She mused, finally looking up at me. “But make it vintage.

90s mum.” She wasn’t wrong. This entire outfit was basic to the point of boredom, but something about how Mum rocked that cardigan spoke to me. She pushed her sleeves up, slightly cropping the length of the sleeves to play on the oversized fit of the jumper itself.

She wore black leggings instead of jeans; currently trendy but once again something my mother wore decades ago on the daily. It was, of course, the CEO who ultimately stole the show. Never in my five years of working at The Compass did I once receive a compliment from our company’s CEO.

Never have I spoken directly to her without her abruptly cutting me off to return to staring at her phone. Until Friday. “Good cardigan.” She said curtly as we ran into each other while waiting for the lift, completely unbothered by my literal awe of her taking notice of my outfit. Sometimes, words don’t even need to be finished to leave a lasting impact.

DAY 6/7: WEEKEND – Turn It Up, Mum. When I wasn’t too busy fantasizing about a post-mortem Grammy’s tribute in Mum’s honour, we finished off our week with her “nice dinner outfit” from May of 1993. Black velvet blazer (also from Sears) tied over a simple slip dress, with sheer black tights, black leather loafers, and a print scarf wrapped around her waist.

Mum and dad were pictured outside of some fancy Italian restaurant, him wearing that iconic 90s dad skinny tie + suit combo and her… being impossible not to stare at. She wore her hair up in the same type of pony we paired throughout the week, but loosened the curls at her face for a softer, more feminine look. Minimal jewellery except for hoop earrings and that good ol’ wedding band.

She didn’t mess around when it came to going out for Mum. This entire outfit was easily the most flattering of the ENTIRE week. Things I borrowed and will now own forever: the blazer (VELVET.

AS IF. ), the nude tights. The low-cut loafers with block heels. The slip dress was a close enough recreation from one of my favourite vintage stores downtown and mum thankfully approved the floral scarf I used to tie around my waste.

Even my underwear matched what she was wearing; a cheeky black lace boy-short that’s been in my drawer since God knows when but still feels modern as hell. I wore this entire outfit out to dinner with friends at a new spot in TriBeCa; the kind of “upscale but still Brooklyn authentic” restaurant where I 100% know people judged my outfit while pretending not to. We had a reservation for 8PM, so obviously got seated at 8: 45 and weren’t ‘all that’ upset when the hostess explained “NYC standards.” “You look different,” Jake said as I slid into the booth next to him. “In a good way.

More… put together? Is that offensive?” I spent the next twenty minutes explaining my week-long mission as my friends trickled into the restaurant, each with their own variation of oohs and ahhs when presented with the plethora of 90s mum outfits I had saved on my phone. “I thought you were wearing vintage Helmut Lang.” Emma exclaimed over the app as she scrolled through pictures, reaching out to pinch the velvet blazer. “This is Emmit’s mum? From Syosset?

THE one with the pumpkin pie that you refuse to eat because it’s literally all veins?” I chuckled and nodded. “She used to be cool back in the day. Way cooler than you think.” Emma flipped through photos of my mum carefully, studying her outfit choice in May of ‘93. “Cool doesn’t expire, Emma.” She paused, tapping at her phone. “This outfit. Slaps.” My entire night was solidified when the sommelier- who was approximately my mother’s age, give or take a few years- stopped by to take our wine order and DID.

A. DOUBLE. TAKE. “I had that blazer,” she said, eyebrows raised as she scanned my outfit. “ANN-TAY-yor, wasn’t it?

1992? 93?” I nodded, completely STARSTRUCK by how this complete stranger had the same blazer that my mother basically lived in for the better part of a decade. “I wore that shit out of existence,” she continued, eyes distant as if she could picture herself 25 years ago in that exact outfit. “Kinda wish I kept some of my clothes from back then…” By the time dinner was over I had three people stop by our table to compliment my outfit (Including the hostess who recognised the brand of my blazer), a server asking where I found “the perfect vintage jacket,” and Emma threatening to have me buy her every single item in my closet so she could recreate her mother’s outfits from the 90s. “I never want you to stop wearing these old clothes,” Mum said when I texted her the final photo. We sent so many side-by-side comparisons of her old pictures and my recreations that day, she was quick to point out how “you look better in them than I did.

Keep the blazer, please. It needs to live in NYC, not in my closet.” THE TAKEAWAYS If there’s one thing dressing like your mum for an entire week has taught me, it’s this: 1. Mum was and will forever be cooler than I give her credit for.

Yes, she wore “mum” clothes. But those “mum” clothes were slim-cut, high-waisted jeans and flattering t-shirts. She paired feminine dresses with Docs.

Statement jewellery with faded tees. She knew how to use clothing to mold her body into trendy, stylish silhouettes without sacrificing comfort. Her style was tight.

And dare I say, trendy as fuck. 2. Old photo albums = pure styling gold.

Before we lived in a world of Instagram and TikTok telling us what to wear next, there were faded pictures of our parents and family members wearing outfits we wish we could raid from their closets. Mine is literally reaching out to her for styling inspiration months after our original project ended. 3.

Thank god for the 90s. Honestly, what a decade for understanding the perfect blend of trendy, comfortable clothing. Mum’s outfits weren’t just aesthetically pleasing, they were easy to move in; ideal for a working mum raising children and maintaining her personal style at the same time.

4. If it’s built well, it’ll last. We’ve all heard the saying; but holy crap does it apply here.

Literally every single piece of clothing I pulled from my mum’s closet is in wearable condition.

Some were worn out (thank you, dinosaur sleeves) but for the most part her clothes are high-quality AND high-fashion.

Win.

Win. 5. It’s not about the individual pieces, it’s about how you style them together.

What made my mother’s outfits so damn iconic wasn’t JUST the individual pieces she chose to wear; it was how she paired them together. That cropped look of leggings with ankle boots. Mum blouse hacked into a crop top.

Balance breast and hips with oversized everything else. It’s still magic. And lastly… Dressing like my mother for an entire week has given me so much more than just a newfound appreciation for 90s fashion.

Seeing her recreated outfits side-by-side with hers made me realise something I hadn’t up until this project; that her identity was more than just “my mum.” Underneath the garden hoes and yoga trousers exists a woman who rocked Docs with slip dresses, knew how to tie a flannel around her waist, and kept every chic black blazer she owned for over thirty years. Scroll through old photo albums with your mum this weekend. I bet she’ll love showing you what she and dad wore to their fifth wedding anniversary like I know mine will.

Trust me.