It started with a rainy Sunday afternoon and a dusty photo album I found while helping my parents clean out their basement. I was home for the weekend, ostensibly to “help” but mostly to raid my mom’s pantry and do laundry for free like the successful adult I pretend to be. Between sorting Christmas decorations and arguing about whether anyone would ever use that bread maker again, I discovered a plastic tub of photo albums I hadn’t seen in years.
And there she was—my mom in her 1990s glory. Picture after picture of her in outfits that could have walked straight off today’s runways. High-waisted Levi’s with a perfect taper. Oversized blazers with strong shoulders. Slip dresses layered over tissue-thin turtlenecks. A rotating collection of statement earrings that would make current Etsy sellers weep with envy. Doc Martens worn with floral dresses. Tiny sunglasses. Scrunchies. Cardigans buttoned only at the top. The works.
“Mom,” I said, showing her a particularly stellar photo of her circa 1994, wearing a chocolate brown blazer over a vintage slip dress with chunky loafers, “you were cool.”
She rolled her eyes, reaching over to close the album. “Those are just old clothes, Harper.”
But they weren’t just old clothes. They were a fashion revelation—proof that my mother, who now lives almost exclusively in gardening clothes and sensible shoes, was once the epitome of effortless 90s style. The woman who regularly asks me if “people still wear jeans” had once been cooler than I could ever hope to be.
That’s when the idea hit me. What if I spent a week dressing exactly like 90s Mom? Not as a costume or some retro caricature, but as a genuine style experiment. After all, fashion is cyclical, and everything 90s is thoroughly back—from slip dresses to square-toed boots to tiny bags that hold approximately one lip balm and half a credit card.
I pitched the idea to Katherine, our editor-in-chief, expecting her to laugh it off. Instead, she nodded thoughtfully. “Interesting concept. Family photo albums as style inspiration. But it needs a stronger angle.” She tapped her pen against her desk. “What if you recreate specific outfits? Find the exact photos and match them as closely as possible?”
And that’s how “I Dressed Like My Mom for a Week” went from a vague concept to a fully approved article with a photography budget and a deadline. All I needed was my mother’s blessing and access to her 90s wardrobe—which, knowing her borderline hoarding tendencies with clothing, likely still existed somewhere in the family home.
“Absolutely not,” was her first response when I called to explain the project.
“Why not?” I asked, genuinely surprised. “It’s a compliment. Your style was amazing.”
“Because it’s embarrassing,” she said. “Those clothes are from another lifetime. Before you were even born.”
“That’s what makes it interesting,” I insisted. “Plus, it’s literally my job to write about fashion. Consider this a professional courtesy interview.”
There was a long pause. “Will there be photos of me in the article?”
“Only if you want. But definitely photos of the original outfits.”
Another pause. “Do I get to approve which photos you use?”
“Within reason.”
I could practically hear her thinking through the phone. Finally: “If I do this, you have to come help me clean out the garage next month.”
And that, friends, is how I ended up back at my parents’ house the following weekend, digging through storage bins and closets to unearth my mother’s 90s wardrobe while she provided running commentary about which items she couldn’t believe she ever wore and which she was still secretly proud of.
Surprisingly, she had kept almost everything. The blazers. The slip dresses. The vintage Levi’s. Even the Doc Martens, still in wearable condition despite being older than my college interns. Some pieces had been moved to the “painting clothes” category, some were wrapped in tissue paper in storage bins, and some—the real treasures—still hung in the back corner of her closet, preserved like artifacts from a particularly stylish archaeological dig.
“I could never get rid of this,” she said, pulling out a black slip dress with delicate lace trim. “Your father bought it for our first anniversary.” She held it against herself, considering. “But I don’t think it would fit me now.”
We spent hours sorting through her collection, matching garments to photos, me squealing with delight at each discovery, her gradually warming to the project as she recounted stories behind certain pieces. The burgundy blazer she wore to her first big job interview. The vintage kimono-style jacket found at a flea market in Chicago. The men’s button-down she stole from my dad and never returned.
By Sunday evening, I had seven complete outfits planned, each based on a specific photo from the 90s. Some pieces came directly from mom’s closet. Others were reasonable facsimiles I’d need to source—either from my own wardrobe or from vintage shops. Mom even agreed to loan me her collection of silver jewelry, most of which had been sitting in her dresser unworn for years.
“Just don’t lose the turquoise ring,” she warned as I packed everything into garment bags. “It was your grandmother’s.” Considering my grandmother had been a bohemian artist with impeccable taste, this felt like receiving the family heirlooms early.
MONDAY: The Power Blazer
The week began with one of mom’s most iconic looks from 1992: an oversized charcoal blazer with powerful shoulders, worn over a simple white t-shirt, straight-leg jeans cuffed at the ankle, and black ankle boots. The photo showed her leaning against a brick wall, looking impossibly cool and slightly intimidating, with chunky silver earrings and her hair pulled back in a low ponytail secured with what appeared to be an actual pencil. Accessories included a chunky silver watch and sunglasses with a subtle cat-eye shape.
Luckily, 90s blazers are so thoroughly back that I already owned something similar. The jeans came from mom’s actual closet—vintage Levi’s 501s that fit me perfectly, making me question everything I know about modern sizing. The pencil in the hair was perhaps a bit literal for 2025, but in the name of accuracy, I slid a black Blackwing pencil into my ponytail and hoped it looked intentional rather than unhinged.
Walking into the Style Compass USA offices, I felt strangely powerful. The blazer’s shoulders made me stand straighter. The vintage denim had that perfect broken-in quality that no amount of artificial distressing can replicate. The chunky silver jewelry felt substantial in a way that my usual delicate pieces never do.
“New look?” asked Simone, our fashion director, as I sat down at the morning meeting.
“Sort of,” I replied. “I’m dressing like my mom for a week. This is her circa 1992.”
Simone studied me appraisingly. “The proportions are excellent. Very Helmut Lang meets American workwear.” Coming from her, this was essentially a standing ovation.
By lunchtime, three different colleagues had complimented the blazer, and one intern had asked where I found the jeans. “They’re my mom’s,” I answered, enjoying the look of confusion followed by envy that crossed her face.
The most surreal moment came during an afternoon coffee run when the barista—a guy with excellent personal style who regularly serves most of the fashion industry from his station at the overpriced coffee shop in our building—actually did a double-take.
“This outfit is fire,” he said as he handed me my cold brew. “Very 90s cool without trying too hard.”
If only he knew just how 90s it actually was.
TUESDAY: The Slip Dress + T-Shirt Combo
Tuesday’s recreation focused on a look from 1994: a black silk slip dress layered over a white baby tee, paired with chunky loafers and ankle socks. This was quintessential 90s layering—that perfect mix of grunge and feminine that defined the era. In the photo, mom had paired the look with a choker necklace (very of-the-moment) and a tiny backpack that couldn’t possibly have held more than a lip balm and a pack of gum.
The slip dress came directly from mom’s closet—the anniversary gift from dad that she’d preserved all these years. It was a bit loose in the bust and a bit short for today’s standards, hitting mid-thigh rather than the more modest midi length currently in fashion. The t-shirt underneath was vintage Calvin Klein from my own collection. I couldn’t find a tiny backpack that matched the original, so I substituted a small crossbody bag that captured the same energy.
This outfit felt both familiar and revelatory—a silhouette I’ve worn in various iterations throughout my career, but with proportions straight from 1994. The slight oversize of the t-shirt under the slinky slip dress created a tension that felt distinctly 90s but also completely relevant to how we dress now.
Katherine stopped by my desk mid-morning. “The slip dress with the tee—that’s a specific reference to something, isn’t it?”
I showed her the photo of mom on my phone.
“Fascinating,” she said. “It’s almost identical to what half the attendees were wearing at that Miu Miu event last month. Your mother was ahead of her time.”
The ultimate validation came during a market appointment at a showroom downtown, where the PR assistant actually took a photo of my outfit “for reference.” When I explained it was based on my mom’s 90s style, she asked if I could send her the original photo for their mood board. Somewhere in heaven, Kurt Cobain was either laughing or rolling his eyes.
WEDNESDAY: Canadian Tuxedo with a Twist
By Wednesday, I was fully committed to the experiment and excited to try one of mom’s most daring looks: the full denim ensemble from 1995. In the photo, she wore high-waisted, light-wash jeans with a matching denim jacket, a black turtleneck underneath, and what appeared to be burgundy ankle boots. Her hair was pulled into a messy bun with face-framing tendrils, and she wore small hoop earrings and a statement belt with a large silver buckle.
The Canadian tuxedo is hardly revolutionary in 2025, but something about mom’s version looked especially fresh. The high waist of the jeans. The slight crop of the jacket. The perfect wash of the denim that looked authentically worn rather than factory-distressed. I borrowed both the jeans and jacket from her collection, grateful that we’re roughly the same size and that she’d preserved these pieces.
“This isn’t exactly office-appropriate,” I murmured to myself as I got dressed that morning, wondering if the double denim might be a bit much for a day that included meetings with two potential advertisers.
But sometimes fashion requires commitment to the bit. I added the black turtleneck (my own), found similar burgundy boots in my closet, and replicated her messy bun as closely as possible. The final touch was a vintage silver belt I found at the bottom of her jewelry box.
The first advertising meeting went surprisingly well. The client, a beauty brand looking to place sponsored content, actually commented on my “refreshing style.” The second client, an older gentleman from a luxury watch company, seemed slightly confused but polite.
But the real test came at lunch, when I bumped into Tyler from our competitor publication—a notoriously judgmental fashion editor known for his scathing reviews and impeccable personal style.
“Harper,” he nodded, looking me up and down. “Bold choice.”
I braced for sarcasm, but instead he continued: “I’ve been seeing workwear denim everywhere in Paris. You’re ahead of the curve for once.” And then, the ultimate backhanded compliment: “It actually works on you.”
I considered telling him I was dressed like my mom from three decades ago but decided to simply accept the rare praise. Sometimes fashion victory comes from unexpected places.
By afternoon, I had received two Instagram DMs from followers asking about the denim set, and one of our junior editors had taken a “fit pic” of me for our office style roundup. If only my mother could see the impact her 1995 Sears catalog purchases were having on fashion industry insiders in 2025.
THURSDAY: Floral Dress with Combat Boots
Thursday’s recreation was perhaps the most quintessentially 90s: a floral midi dress with spaghetti straps, worn over a white t-shirt, paired with black combat boots and a plaid flannel tied around the waist. In the photo, taken around 1996, mom stood in front of a record store looking effortlessly cool in that distinctly 90s way that mixed feminine and grunge elements.
This was the hardest outfit to recreate exactly, as the dress was long gone—apparently sacrificed to a paint spill during a home renovation project years ago. But mom and I found a similar vintage floral dress at a thrift store near their house. The combat boots were her actual Docs, preserved in surprisingly good condition. The flannel came from my dad’s side of the closet—apparently some things never change, including his adherence to the same style of plaid shirts he’s worn for 30+ years.
Walking to the subway that morning, I felt like I was in a time warp. The combination of floral dress and heavy boots created that distinctive 90s silhouette that’s both pretty and slightly aggressive. The flannel around my waist was purely decorative in April weather, but visually essential to the look.
This outfit received the most immediate reaction—not all of it positive. My downstairs neighbor, an older woman who frequently comments on my “unusual clothes,” actually stopped me in the hallway.
“Are you in a play?” she asked, genuinely concerned.
At the office, reactions were more appreciative. Emma from the beauty department immediately recognized the reference. “Classic 90s,” she said approvingly. “Very Angela Chase from My So-Called Life.”
What surprised me most was how comfortable the outfit felt, despite being far from my usual aesthetic. The boots grounded the otherwise sweet dress, creating tension that felt modern despite its distinctly 90s origins. The proportions—midi length, slightly oversized tee underneath, chunky boots—created a silhouette that played with feminine and masculine elements in a way that still feels relevant.
The real shock came during an afternoon coffee meeting with a Gen Z influencer we were considering for a collaboration. She took one look at my outfit and gasped audibly.
“Your fit is literally everything,” she said, already pulling out her phone. “Can I take a pic for my stories? This is exactly the vibe I’ve been trying to create.”
If only she knew she was essentially taking style notes from a suburban mom who bought that dress at JCPenney while pregnant with her second child.
FRIDAY: The Oversized Cardigan + Leggings Look
Friday brought what mom referred to as her “everyday mom uniform” circa 1997: black leggings with an oversized cardigan, ankle boots, and a simple white t-shirt. In the photo, she wore this while standing in our childhood kitchen, looking impossibly chic while apparently in the middle of making dinner. Her hair was pulled back in a simple low ponytail, and she wore minimal jewelry except for small hoop earrings and her wedding ring.
This outfit felt the most timeless of all the recreations—a combination that wouldn’t look out of place in any decade from the 90s forward. But what made mom’s version special was the proportions and details: the slightly cropped length of the leggings, the chunky knit of the cardigan, the way she had pushed up the sleeves to create volume.
The cardigan came from her current closet—apparently this piece had made the transition from “fashion” to “comfort” in her wardrobe rotation, now worn for actual warmth rather than style. The leggings were my own, though I had to roll them slightly to match the cropped length in the photo. The white tee and ankle boots were also mine, similar enough to the originals to capture the essence of the look.
Walking into the office on Friday, I expected this outfit to go relatively unnoticed—it was close enough to current athleisure trends to blend in. Instead, it generated perhaps the most interesting responses.
“There’s something different about this one,” said Katherine when I stopped by her office for our weekly check-in. “It’s simple but has perfect proportions.”
She was right. Despite being the most basic outfit of the experiment, it had a balance that felt intentional rather than thrown-together. The slightly cropped leggings created a specific silhouette with the ankle boots. The oversized cardigan provided structure while maintaining comfort.
At lunch with the social media team, our newest coordinator—a recent graduate with a keen eye for aesthetic—studied my outfit carefully.
“It’s like elevated normcore,” she said finally. “But make it 90s mom. I love it.”
The greatest compliment came from the most unexpected source. While waiting for the elevator at the end of the day, I bumped into our company’s CEO—a terrifying woman in her sixties who exclusively wears Dries Van Noten and has never once commented on my appearance in the five years I’ve worked here.
“Good cardigan,” she said, nodding at my outfit before returning her attention to her phone.
From her, those two words carried the weight of a standing ovation.
WEEKEND: Mom’s “Going Out” Look
For the weekend finale, I recreated what mom called her “fancy dinner outfit” from 1993: a black velvet blazer worn over a simple slip dress, with sheer black tights and heeled loafers. In the photo, she and dad were dressed for what appeared to be an anniversary dinner, him in a suit that still somehow looked awkwardly fitted despite presumably being tailored, her looking like she could walk a runway at any moment.
The velvet blazer was another preserved treasure from mom’s closet, maintained in excellent condition and smelling faintly of the Shalimar perfume she wore throughout the 90s. The slip dress was a vintage find that closely matched her original. The sheer tights and heeled loafers came from my own wardrobe—luckily, these are classic pieces that haven’t changed dramatically over the decades.
I wore this ensemble to dinner with friends at a new restaurant in Tribeca—the kind of place where people definitely judge your outfit while pretending not to notice what you’re wearing. The reservation was for 8 PM, which in New York means you actually get seated at 8:45 and pretend that’s completely normal.
“You look different,” said my friend Jake as I slid into the booth. “More… polished? Is that offensive?”
I explained the week-long experiment as my other friends arrived, each with their own reactions to the 90s mom aesthetic.
“I seriously thought you were wearing vintage designer,” said Emma, reaching out to feel the velvet blazer. “This is Emmett’s mom’s? From Long Island? The one who makes that brutal pecan pie at Thanksgiving?”
I nodded. “She wasn’t always the suburban mom you know now. She used to be cool.”
Emma studied the photo I showed her on my phone. “She’s still cool. This outfit slaps.”
The most surreal moment came when the sommelier—a woman probably around my mother’s current age—stopped by our table and did a double-take at my outfit.
“I had that exact blazer,” she said, momentarily abandoning her wine description. “Ann Taylor, right? 1992 or 93?”
I nodded, stunned.
“I wore it to death,” she continued nostalgically. “Makes me wish I’d kept more pieces from that era.”
By the end of dinner, three separate people had stopped by our table to compliment the outfit, one server had asked where I found “such a perfect vintage blazer,” and Emma had made me promise to help her recreate a similar look from her mother’s 90s photos.
When I sent mom a photo of the final outfit, her response was both surprising and touching: “You wear it better than I did. Keep the blazer. It belongs in NYC, not sitting in my closet in Long Island.”
WHAT I LEARNED
After a week of dressing like my mother, I’ve come to several conclusions:
1. My mom was significantly cooler than I ever gave her credit for. Her 90s style wasn’t just “mom clothes”—it was legitimately fashion-forward, with proportions, silhouettes, and combinations that feel completely relevant today.
2. Vintage family photos are an untapped resource for style inspiration. While we’re all looking to Instagram and TikTok for the next trend, there’s something powerful about finding style inspiration from your own lineage.
3. The 90s truly were a sweet spot for wearable fashion that balances comfort and style. Mom’s outfits weren’t just visually appealing—they were functional and comfortable, designed for a woman who was working, parenting, and trying to maintain her identity all at once.
4. Quality pieces really do stand the test of time. The fact that so many of mom’s garments are still wearable after 30 years speaks to both the quality of construction and the timelessness of her choices.
5. Style is as much about proportion and silhouette as it is about specific pieces. What made mom’s outfits special wasn’t necessarily the individual garments but how she combined them—the slightly cropped length of leggings with ankle boots, the oversized blazer with slim jeans, the tension between feminine and masculine elements.
Beyond these style lessons, the experiment gave me something unexpected: a new appreciation for my mother as a complete person with an identity beyond “mom.” Somewhere under the gardening clothes and practical shoes is the woman who wore Doc Martens with slip dresses and knew exactly how to tie a flannel around her waist for maximum effect.
When I showed her the final article draft and photos, her reaction surprised me.
“I forgot who I used to be,” she said quietly, studying the side-by-side comparisons of her 90s photos and my recreations. “You forget parts of yourself when you become someone’s mom.”
We spent the next hour going through more photo albums, her pointing out outfits I hadn’t noticed, telling stories about where she wore them, what music was playing, what she was feeling. It was the first time I’d ever really seen her as someone with a complete life and identity before she became My Mom.
“You should wear your old clothes again,” I told her. “The blazers, at least. They’re completely back in style.”
She laughed. “Maybe I will. Your father would have a heart attack if I showed up to bridge club in that slip dress, though.”
I’m keeping several pieces from the experiment in my regular rotation—the vintage Levi’s that fit better than any modern jeans I own, the velvet blazer that goes with everything, the chunky silver jewelry that makes even the simplest outfit feel intentional. They connect me to a version of my mother I never knew but somehow recognize in myself.
So here’s my challenge to you: Raid your family photo albums
