It began with one rainy Sunday afternoon and an old dusty photo album I stumbled across while helping my parents clean out their basement. Home for the weekend to “help” (meaning: eat my mom’s food and do laundry for free like the successful adult I am), I had spent several hours excavating through piles of old Christmas lights and sad stuffed animals. Mid-way through arguing over who really needed to keep that bread maker, I unearthed a forgotten plastic tub filled with photo albums from the pre-smartphone era.
And there she was. My mom in her 19-whatever glory. Snap after snap of her wearing things I still wear today.
High-waisted Levi’s that actually tapered at the ankle. Oversized blazers with broad shoulders.
Slip dresses worn over delicate white t-shirts.
An ever-changing assortment of oversized earrings that would make Etsy sellers jealous today. Docs with flowery dresses. Tiny sunglasses.
Scrunchies. Cardigans that were never buttoned all the way. The works. “Mom,” I declared, flipping to an especially stellar photo of her circa 1994, black blazer layered over a vintage slip dress, chunky loafers, “you were cool.” She rolled her eyes, leaning over to close the album. “Those are just old clothes, Harper.” No, they were not old clothes.
They were a gateway into understanding how my mom—a woman who currently lives in leggings and Loft sweaters and Kinleys—was the coolest mom of all time. Turns out that woman who regularly asks me if “people still wear jeans” rocked the 90s like a professional. All of this led to the idea: What if I spent an entire week dressing exactly like mom did in the 90s?
Sure, some of it would have to be re-created (no way was I wearing actual mom jeans), but the spirit of the outfits would remain intact. Plus, everything 90s is having a major moment right now—from slip dresses to square-toed booties to tiny crossbody bags that can fit approximately one lip balm and half of your credit card. I pitched the plan to Katherine, our editorial director, half-expecting her to laugh me out of the office.
Instead she nodded enthusiastically. “Interesting angle. Family photo albums as styling inspiration. But maybe leaning too soft.
What if instead of general outfits, you recreate specific outfits? Pull the exact photos, then find as close to an identical match as possible?” And just like that, “I Dressed Like My Mom for a Week” went to go from half-formed twitter thought to officially assigned article with photography budget and deadline. All I needed was buy-in from my actual mother and access to her ancient closet, which, knowing her hoarder tendencies when it came to clothes, undoubtedly housed half of her actual outfits from the 1990s. “I don’t want to do that,” she told me over the phone when I first called to explain what, precisely, I was asking her to do for me. “Are you crazy?” “No, it’s fine,” I assured her. “It’s flattering, really.
You had great style.” “It’s embarrassing,” she replied. “Those clothes were sooooo outdated.” “WHAT??? They’re coming back!” I shouted into the phone, scrolling through TikTok evidence. “Remember slip dresses? Square toe booties?” She sighed. “When you put it that way, I guess it could be fun.” Pause. “But you better be interviewing me for this.
This is gold.” It’s a testament to just how quickly fashion trends cycle through these days that many of my mother’s favorite outfits from the early 90s could pass for things I’d wear today, given the right pieces. With the help of some serious closet digging, mounds of google-stored photos, and weeks of self-reflection, I’m giving you my favorite recreations from the week I dressed like my mom in the 1990s. Behold: If your parents were cool in the 1990s, here’s how to relive their best looks through your own wardrobe.
SATURDAY: The Slip Dress I Wish I Owned One of my personal favorite outfits from my mother’s younger days: A black slip dress worn over a white tank top, high-waisted skinny jeans, and a towering pair of Frye boots. Mom in circa 1996, before actual children but after college when she was feeling her most ambitious-and-mostly-employed-self. The slip dress, sadly, was long gone from my mother’s closet (apparently painted out of existence by our borderline alcoholic family dog), but we did find a similar slip at an adorable vintage shop near their house.
The jeans were an actual pair from mom’s closet—the ones I wore throughout the project that fit me inexplicably better than my own jeans. The Frye boots? Also hers.
She kept the dusty originals from her twenties, still in nearly perfect condition. “That’s when I wore combat boots with EVERYTHING,” she chuckled as I slid into her outrageously high boots. Fun fact about my mother: she basically wore the same boots with every outfit she put together for our year-long experiment. As for how this old-meets-new outfit was received: An embarrassingly large amount of praise.
Interns stopped me in the halls to ask where I got the dress. Colleagues at meetings would compliment my “statement jeans.” My boss told me I “had great legs” for the first time in my career. She was right about one thing, though.
My coworkers did actually stop to take photos of me in this outfit. Not because it was a costume (though it sort of was? ), but because it looked like I genuinely could have trotted this exact outfit out of a vintage shop that afternoon. Which, come to think of it, I kind of did.
SUNDAY: Workout Clothes were serious about rocking my mother’s vintage Levi’s 501s that she kept from her youth. Stomping around the office in her actual high school jeans may have given me an unrealistic viewpoint on how this look was received—we were all too busy laughing at my Carlton Dance-worthy pants to pay much attention to the actual outfit, I’m sure—but I have never felt more powerful walking into work. MONDAY: Button Down + Jeans + Docs Day one of dressing like mom meant channeling one of her oldest looks, from way back in 1992: an oversized charcoal blazer with broad shoulders, white t-shirt, skinny jeans cuffed at the ankle, black ankle boots… and, of course, Docs.
The photograph I chose was her at a NYC music festival, leaning up against a brick wall with half of her outfit smooshed up against the bricks, black chunky earrings, and her hair tied back with… an actual pencil. Accessories included a thick silver watch and tiny sunglasses. Luckily, blazers from the 90s are so back right now that I actually own something similar.
The jeans were borrowed from mom’s closet—the real deal, vintage Levi’s 501s that actually fit me better than my own pants, which is saying something. The pencil in my hair was maybe a bit too on-the-nose for 2025 standards, but whatever. For authenticity’s sake, I shoved a black blackwing in my hair and called it a day.
I felt unstoppable walking into work that day. Seriously, I blame that blazer for me accidentally dominating the weekly company meeting. The vintage denim looked (and felt) like it had actually been worn instead of artificially distressed by some teenager with a cheese grater.
And those silver jewelry pieces were so heavy it literally changed my posture, wearing them instead of my typical daintyhipster crap. “New look?” our fashion director, Simone, asked as she slid into the seat next to me at the morning meeting. “Sort of,” I replied. “Trying to dress like my mom for a week. Thought I’d start with this, circa 1992.” She inspected me for a moment. “Your proportions are on point. Very Helmut Lang meets American workwear chic.” It’s office code for: standing ovation.
Three different people asked me where I got the blazer that day. I beamed proudly as my coworker / neighbor / Facebook friend paused our brainstorming session to message me on Instagram, asking where the heck she could find those jeans. Our barista literally did a double take. “I love your outfit,” he said as he handed me my iced coffee. “Sooooo 90s, but not try-hard?” If he only knew.
TUESDAY: Dad Jeans + Slip Dress 101 The theme for Tuesday? 1994, thanks. Mom nailed the slip dress over t-shirt combo so perfectly that I actually had to improvise here and there to keep things interesting for the reader.
Slip dress? Check. She had that one covered.
Tiny black leather backpack? Um… no. Instead I opted for a similar black slip dress from Mom’s closet (the one she refuses to get rid of because “your father bought it for our first anniversary!”) and found a reasonable replica from one of my own closet’s sundresses.
That left us with the jeans, t-shirt, and boots to play around with. The jeans were, once again, borrowed from mom. Dad jeans are the one type of jean both my mother and I seem to have miraculously maintained from the 90s—probably because we actually wore them into some sort of shape back then, unlike today’s instantly-distressed-at-the-manufacture fashion jeans.
The booties were also borrowed from the mother of style—I know this for a fact because she huffed angrily at me when I tried on her booties and she realized they were “still too big.” Objectively one of my favorite silhouettes—I’ve been rocking the shirt-under-dress combo since college—I’ve never felt better putting this outfit together. Something about that slight oversize of the t-shirt underneath the figure-hugging slip dress feels so 90s, yet totally on brand for how we wear clothes today. “How did you find that slip dress?” my boss asked me at lunch, pausing our Power Point session to grab a photo of me for her own notebook. “It’s vintage,” I replied. “Vintage as in…” “I dressed like my mom in the 90s for a week,” I said before waving her over to see where I bought the jeans. “That’s incredible,” she murmured, clearly more impressed than I think she let on. “You should totally write a whole article about this.” THREE HOURS LATER: Here we are. WEDNESDAY: Distressed Jeans + Vetted Blazer Wednesday came and went in a blur of denim-on-denim styling opportunities, none better than my mother’s iconic, slightly DIY Canadian tuxedo getup circa 1995: high waisted, light-wash jeans + matching jacket, black turtleneck, red ankle boots, and the infamous messy bun with face-framing hairs still visible / tie together with an actual PENCIL.
While I was unable to replicate mom’s actual jeans & jacket combo thanks to unfortunate incidents involving bleach and a parking ticket several decades ago, both items were luckily preserved in her attic wardrobe, ready to be worn by their holy savior. “This isn’t office appropriate, Harper,” I warned myself as I put on the jacket. How would clients react to my double denim bravado? Our test appointments with advertisers were Monday and Tuesday.
Would they think we weren’t taking this partnership seriously if I showed? Too late for doubts. I was wearing the jacket and had mentally committed to the leather pencil hair tie.
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Lunch that day consisted of me pointing out the likeness between my outfit and my mom’s outfit from twenty-eight years prior to anyone who would listen—and nobody could stop staring. “That outfit is fire!” our barista said as he slid my venti iced coffee across the counter. “So 90s, but in a cool way?” If they only knew how extra 90s it actually was. THURSDAY: Boyfriend Tee + Midi Dress Vintage Shopping Find. Floral midi + black t-shirt.
Combat boots. A plaid flannel tied around the waist, because what’s a 90s dress sans-flannel? This was perhaps the most authentically-90s look we pulled from mom’s archives—front windshield of the Caravan, she stood in front of an old Record Stop shop while proudly modeling her Jordache-esque ensemble circa 1996.
We lost the dress a few years back. Paint project gone wrong. Named cat.
Life. But were fortunately able to scoop up something similar from Mom’s local Goodwill, bless her soul. The combat boots were also borrowed from her closet—I know this for a FACT because she said as much when she tried mine on and they didn’t fit her “correctly” anymore. “The flannel is from your dad’s side of the closet,” she laughed when I stuffed The Greatest Shirt Known To Man wrapping garment behind my waist.
And yet it still felt like me. Mom raised me right. FRIDAY: Mom’s Literal Mom Uniform Mom’s Everyday Mom Uniform, circa 1997: black leggings with oversized cardigan, ankle boots, and white tee.
Judging by photo evidence, she was making dinner in our old kitchen because 1. SHE HAD ON LEGGINGS TO COOK DINNER IN AND 2. THAT WAS QUITE Literally my mother wearing the leggings she wore every single day while raising me and my brother.
And they looked freaking adorable on me. Despite being leaps and bounds away from my personal style—I typically reside in slightly stirrup jeans and dryly witty tee-shirts—I couldn’t believe how much I loved this entire outfit. The slightly cropped leggings with ankle boots, the soft yet chunky knit of the cardi, even pushing up the sleeves to give it some volume. “What’s different about this one?” my boss asked me during our weekly check-in, fingers steepled under her chin as she studied me. “I don’t know,” I replied, wondering internally if my body was actually lying to me about how good I looked today. “Seemed pretty basic?” “No,” she said, shaking her head. “It’s simple, yes.
But everything fits you. Perfect proportions.” She’s never actually *said* that to me before. DAYTIME SATURDAY: Leather Jacket Love It was black leather jacket weather at the office that day, which, let’s be honest, is basically every day of the year in New York.
For authenticity’s sake, I actually wore mom’s real leather jacket from 1993 while recreating her weekend “What I Wore To Run errands And Meet Up With Friends” look: black slip dress, chunky neutral jewelry, white tank top. The jacket was… life changing. As it turns out, mom was ALSO INTO oversized leather jackets with heavy shoulders back in the day too?
Who knew! ? Someone who clearly knows a ton about style sent me this photo of my outfit with the note “THIS. IS.
GENIUS.” Was it a cop-out to wear her jacket? Sure. Did anything about this outfit actually fit in the 90s?
Also sure. Dusk-hued SATURDAY: How to Rock Mom Jeans and a Slip Dress in Public My fave. We tried.
So hard. To find you this exact velvet blazer Mom wore to dinner with Dad in 1993. Alas, we came up empty.
But a quick scroll through Anthro solved all of our problems and we found this bad boy, which Mom approved of via text. Slip dress? Check.
Mom actually kept thedress she wore to Anniversaries With Dad shoved in her closet for when grandchildren decide they want photos taken with their Nana. She never wanted to part with it, she told me. Sheeled Loafers?
Um… check? Mom’s hadn’t quite made the jump to loafers back in the day, but these babies from Target are basically mom quality. Plus, loafers.
Pure White Tank top? Holy crap, check. Mom had this.
The real star of the show? Mom’s blazer. That, and we actually got her husband to take photos of me in the outfit while recreating their actual wedding anniversary photo.
They were *thrilled* to participate. “What are you doing?” I asked, hands on hips. “Photos, obviously. For your stupid project,” he replied, smiling. “Stupid” is quotes because his exact words were, “This is the coolest thing you’ve ever done.” And that, dear reader, is how I spent a week dressed like my mother in the 1990s. WHAT I LEARNED FROM DRESSING LIKE MY MOM If there’s anything I learned from a week of rocking my mother’s actual wardrobe from twenty, thirty, FORTY years ago, it’s this: 1) My mother was cooler than I ever realized.
She wasn’t wearing “mom clothes” when she rocked stiff-shouldered blazers with bootcut jeans and quirky accessories. She was wearing incredibly on-trend outfits that have come back into style dozens of times since she reluctantly retired them from her closet. 2) OLD PHOTOGRAPH Albums are an untapped goldmine of style inspiration.
Stop scrolling through Instagram—what you’re looking for is probably in your parent’s basement. 3) The 90s were peak attire for getting both dressed up and DOWN. Cohesive outfits that wouldn’t look *too* out of place in any era from the 1990s on, but had that something extra that made mom stand out wherever she went.
4) Well-made pieces really do stand the test of time. Literally all of my mom’s clothes are still in wearable condition after upwards of 30 years. Gah, her closet.
5) It’s more about fit and silhouette than anything. Why did my mother look so badass in clothes that I swear should have been retired with tubed skirts and butterfly clips? Because she knew how to mix things in just the right way.
That feminine, tight slip dress with slightly cropped leggings and ankle boots. The ever-present flannel around the waist, because … evolution?
Honestly, between learning how to properly tie a scarf to channeling my inner 90s mom, I’d say I found a lot more than just outfit ideas when I rifled through my parent’s closets.
I found a new appreciation for my mother. Not as MY mom, but as a woman with a style of her own who somehow managed to both seamlessly transition into motherhood while maintaining the spunk and spirit she clearly possessed twenty years ago. Hell, buried underneath all of those rationalized regrets and poorly chosen food choices are reminders that she was kick ass in the 1990s—and still kind of is today. “It’s been fun reliving my glory days,” she told me as we paged through more photos, her reminiscing interrupted only by bursts of, “Oh my God, Harper.
Remember when we?? ?” and “HOW DID I EVER FIT IN THESE pants? ?” “So you should dress like your old self more often,” I said, snapping photos of her wearing her fav boots from CVS in the makeup aisle. “I should,” she agreed, “but I’m way too old to pull off that velvet blazer without looking like I work at Anthropologie.” “It’s AnthroCHIC,” I reminded her. “And you rock Docs with every outfit. Literally.” She laughed. “True.” Sure, she kept the leggings. And the ball caps.
And the Uggs. She also kept a treasure trove of wearable outfits from decades past that she was more than happy to farm out to her offspring, once given the chance. And now, some of them belong to me too.
Try it. You’ve got family photo albums to rifle through anyway.
