I Asked 5 Women to Find and Wear the Oldest Thing They Own

The outfit I remember most distinctly from high school featured a short-sleeved blazer I bought at Loehmann’s. It was mud brown, had puffy sleeves and a peter pan collar, and I wore it with tight boot-cut jeans and purple slides. Believe me when I say I thought I looked incredible and would sooner leave the house in a bathrobe today. In fact, I’d barely even wear an outfit from college today. That’s how low my tolerance is for appropriating my sartorial past.

Maybe that’s true for most people, because when Tracee Ellis Ross wore a shirt from high school to a fancy shmancy polo match in October, several media outlets wrote whole stories about it. Never mind what that says about our news cycle; what’s clear is wearing old-ass stuff is the new sustainable power move. And I don’t mean vintage-old, I mean bought-it-at-BP-in-2006 old. Much chicer.

(I’ll also take those Céline pants.)

As a person who recreates her sense of style on a near constant basis — and one who’s moved 10 times in as many years — I’ve mostly shed all my old duds. It’s for the best, swear. So in my eagerness to see this power move proliferate, I sought out a bunch of stylish people who could play it better than me. Enter Yaminah, Juliana, Jayna, Katie and Jamie, who kindly heeded my request to root around in their closets for the oldest item in there and give it a modern whirl. The results below are a treat to behold. Henceforth, we shall call this Ross-ing.

Yaminah Mayo

Yaminah is the founder of the blog Spicy Mayo.

Vintage overalls — similar style here, Zara shoes. vintage Levi’s men’s jacket — similar here

What’s the item you’ve had in your closet the longest?

My white cord overalls. They aren’t the oldest but they’re up there.

When did you buy them and why? How did you imagine you’d wear them then?

I bought them when I first moved to NYC because I wanted to “upgrade” my style, but I was just too scared to wear them, so they collected dust, hence the lint (lol). I imagined wearing them over sweaters and shirts with chunky boots because I thought that was the epitome of New York fashion. A simple mule and/or loafer is how I prefer to wear them now.

Why have you kept them so long? Have you been through phases with them?

I haven’t been through many phases because they’re corduroy, so I can really only wear them when it’s cold. I did try to wear them this summer with no shirt and no bra. I nearly had a heat stroke but my side boob was on POINT!

How does it feel to wear them now?

I love them because I can wear them a million ways. I can wear them with my vintage shearling coat and it’s a look. I can wear them with a wool overcoat for a more “pulled together” look. If I’m channeling a Nancy Meyers film, I can wear my overalls under a white turtleneck. If you want to look like your life isn’t a mess, I’m telling you, wear white-on-white. HA!

Vintage overalls — similar style here, vintage Levi’s men’s jacket — similar here

Juliana Salazar

Juliana is a freelance writer, stylist, brand consultant and one half of Moonlight Mile

What’s the item you’ve had in your closet the longest?

I’ve made four different attempts at cleaning out my closet in the last few months and these yellow Rag & Bone silk pants are now the oldest thing to have survived them all.

When did you buy them and why? How did you imagine you’d wear them then?

I bought these in 2010 because they were on super duper sale. I think I paid $50 for them. At the time, Rag & Bone was having a moment, so I think I was slightly blinded by the label, but also, I’m a sucker for a good sale. I didn’t think about how I would wear them. I tend to be very impulsive and was just like, “What a deal!!!”

Why have you kept them so long? Have you been through phases with them?

Every time I considered getting rid of them I thought, “Maybe one day I’ll wear them,” and I actually did/do! Honestly, I think I’ve worn them more in the last two years than I ever did when I first bought them.

How does it feel to wear them now?

It feels like I want to give myself a pat on the back for such an accidentally great (and economic) purchase. I love the color, their movement, and how they give an outfit an instant burst of something special. I think I love them now more than ever.

Jayna Maleri

Jayna is the Editorial Director at Madewell.

What’s the item you’ve had in your closet the longest?

An APC button-front denim mini dress with patch pockets and short sleeves.

When did you buy it and why? How did you imagine you’d wear it then?

I’m pretty sure I bought it in 2002, and I know it was at the original Bird, which was on 7th Ave in Park Slope. I lived a few blocks away at the time and was always stopping by to try things on and then get sad that I couldn’t afford them. I was in there being a sad sack and the woman who was working was wearing it with jeans and clogs and she just looked like such ‘70s ceramicist perfection. I remember asking where she got it, getting stressed when she showed me that they only had a couple left, and deciding that I had to buy it immediately. I wanted to wear it just like she did, with jeans and clogs. (I honestly didn’t realize it was a dress until I saw someone wearing it as one at an APC sample sale years after I bought it.)

Why have you kept it so long? Have you been through phases with it?

I haven’t worn it in probably four years? But I love catching a glimpse of it in my closet, with its little annoying buttons and those cute puffy sleeves. I think I keep it because it was such a huge part of my wardrobe for a number of years. I would layer a thermal under it, wear my favorite jeans and a pair of navy Sven clogs and just really feel like the version of myself I wanted to be. I still feel like that version of me is a keeper, so the dress is a keeper as well. I should note that I am not someone who hangs onto clothes – I do a closet overhaul twice a year and am pretty ruthless about separating the wheat from the chaff, so the fact that I still have this piece says a lot about my enduring love.

How does it feel to wear it now? Do you love it/hate it?

It feels very fun to wear it now! Like I’m playing dress up as my younger self! I tried it a few different ways at first, but just kept coming back to the classic uniform: dress on top, jeans on bottom, shirt layered underneath. I’m going through a loafer phase right now so I skipped the clogs (sorry clogs, I still love you forever!), and I’m also going through a phase where I match my socks to my hat (nerd!), but beyond those little style tweaks, this really feels very true to the way I used to wear it.

Katie Sturino

Katie is the founder of Megababe and The 12ish Style.

What’s the item you’ve had in your closet the longest?

These black logo Dior moon boots.

When did you buy them and why? How did you imagine you’d wear them then?

They were a totally splurge when I was 22 and brand new to New York City and very into logos. I imagined that my soon-to-be banker husband would whisk me away to Aspen and I would blend right in. (He never showed up, by the way, and I have still never been to Aspen.)

Why have you kept them so long? Have you been through phases with them?

I don’t know, they were a real splurge! I feel guilty. They remind me of a different time in my life. They are ironic?

How does it feel to wear them now?

It’s funny to wear them because I can see exactly who I thought I would be when I bought them, but paired with this “athleisure” look, I might actually dust them off (literally, they have dust on them) and break ’em out this winter!

Jamie Hunter

Jamie is a fashion brand consultant.

What’s the item you’ve had in your closet the longest?

This stretchy boiled wool long sleeve turtleneck Haider Ackermann dress.

When did you buy it and why? How did you imagine you’d wear it then?

It was one of the first “important” things I bought for myself when I started working at Bergdorf Goodman. Haider is one of those designers you always aspire to wear — nothing he makes is trendy; he kind of operates parallel to most with his own identity.

I wore it then as I do now: with a pair of boots and maybe some fun earrings or a red lip.

Why have you kept it so long? Have you been through phases with it?

It’s something I will never get rid of. It’s structured beautifully and is quite flattering on the body. But I definitely used to wear it more six years ago than I do now.

How does it feel to wear it now?

I still love it.

Photos by Oriana Layendecker. You can follow her on Instagram @orianamarie

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  • Erin

    this blew me away! all such genuinely stylish women, all in a very individual, self-expressive way. LOVE

  • Eliza

    that Haider dress is truly fabulous

  • What a great idea to do this piece! Loved it, Haley.

  • What fun idea! I’m going to have a rummage in my closet to find the oldest thing I own. I’ll be gone a while.

  • Aleda Johnson

    Is that a hot dog purse? Please tell me that’s a hot dog purse.

  • ladybirda

    2002? Get off my lawn. I just dusted off a pair of Doc Martens I’ve had for 20 years, I bought them in high school because they came with free tickets to a music festival. Combat boots are having a moment! I wore them with an oversize cardigan and felt very Angela Chase.

    • Millie Lammoreaux

      I truly think combat boots are never out of style! But, Angela Chase and Courtney Love were my icons growing up, so I’m clearly speaking from a place of lifelong devotion.

      • Kiks

        Last year my best friend tried to tell me my combat boots were
        out of style and I almost disowned her. I wear them in every season and with everything. The soles have almost disintegrated and when they do I will get them re-soled and wear them until I am buried in them.

    • Adrianna

      Teen of the late 90s and aughts here. My sister and I referred to those as “Daria boots”

    • Anne Dyer

      Yes! My sister wore navy Docs to match her navy bridesmaid dress at my wedding. My mom went crazy but I fucking loved it!

    • beckly

      I’ll see ya and raise ya. I’m still wearing the men’s flat black winkelpicker shoes with cowboy stitching I bought for a wedding in 1987. I wore them with a chiffon baby doll dress and black fishnets. They’ve lasted waaaaaaaay longer than the marriage 🙂

      • ladybirda

        Touché. For me to go that far back I would have to wear something I owned when I was in kindergarten. I was KonMarie-ing my jewelry this weekend and found a Mickey Mouse gold bead bracelet I had when I was 3 but it doesn’t quite fit on my wrist now, LOL. I do still own the tshirt I came home from the hospital in, it’s on a babydoll of mine that I passed down to my sons.

        • beckly

          Wow. That’s how to repurpose clothes that no longer fit! I hope the Mickey Mouse bracelet finds a suitably grateful recipient!

        • Charlie

          Keep the Mickey Mouse gold bead bracelet! The hair pin I was talking about is a gold Minnie Mouse one. 🙂

  • Millie Lammoreaux

    This article just has me thinking of all the clothes I’ve gotten rid of that I wish I still had! In particular, I’m daydreaming about my first “boyfriend” style sweater that I bought twenty years ago, in the 8th grade. It was a men’s size large, forest green, thick cotton pullover from the GAP that I wore every single day with a pair of ragged JNCOs. I wish I had it right now — I’d ditch the hemp necklace and pair it with faded black mom jeans, a pair of ankle moto boots and a mustard-y khaki trench. Sigh!

    • Danielle Cardona Graff

      Same! And it’s so annoying when I get rid of something (After at least months of boredom from said item) and then a lightbulb idea comes up after the fact around that item. 🙁

    • Syona

      I think I still have that sweater…

  • laoonatic

    Haha my wardrobe is full of “oldies but goldies”. Well, not that old, because I’m not that old, but I think I still have stuff from middle school. My mother still makes most of my clothes and so I’m emotionally attached to them. It’s hard to let go of them when I know we really thought of the model and chose the fabric and all.

  • Adrianna

    I still wear the leather jacket I received when I was 12. (I’m 28.) I wore it today! I basically wore it every single day in high school. I refused to wear an appropriate coat in the 20 degree winters of Pennsylvania. I never really cared for its simple, boxy silhouette because it doesn’t really flatter my figure. But it was the closest I could get to wearing something studded in my conservative house, and it has the perfect pockets to store my wallet and phone on my chest.

    Parts of the leather are so worn that it turned into suede. My mom wishes I’d stop wearing it in public because there is a giant hole in the armpit. The other day I could have sworn that I got a whiff of the cat pee I tried to remove over ten years ago.

    I don’t necessarily have a lot of nostalgia or love for it. It reminds me of darker times in my life, and of a time where I couldn’t afford the leather jacket I really wanted. But maybe that’s why I still own it.

    • ByeBeckz

      omg I still wear a leather jacket that I got when I was 11 too! Since then my parents have given me new ones and I try to wear them- but nothing is as cool and fitting as my original one! The elbows have slowly worn away but it’s in perfect condition otherwise- never giving it up.

    • jiggahava

      My oldest item is also a leather jacket! My mom bought it for me at 15 and 20 years later I still wear it on the regular. It is definitely a treasured piece.

  • TherapyCranes

    This is disappointing. I have tshirts in my closet from when I was 6 or 7.

    • Frankie

      This is disappointing. I have onesies in my closet from when I was 6 months old. Please, lighten up. The point was to actually wear the items still in their closets.

      • ByeBeckz

        I think she clearly meant she still wears them- as do I. I have some t-shirts from dance classes from when I was 5-7 and I still wear them regularly around the house.

      • TherapyCranes

        Yes, I do wear them. And I said it light heartedly. Yeesh.

  • Laura

    I have light colored denim Gap overalls in mint condition that I still wear – I bought them @1992 – I was @ 24. I kid you not. The best thing about them is that they are xs and still fit baggy 🙂

  • Danielle Cardona Graff

    I have a a grey muscle tee (I think originally was black) originally belonging to my Father since before I was born (1984). It is worn so thin, and stretched out so much, that it lays on my body like a beautiful flowing gauze sack. There’s even a giant hole in the back, completely sheer, and the color fades from a darker grey almost black, to a lighter slightly less transparent grey at the bottom. I tell myself it inspires the deconstructed look of Comme Des Garcons….my Mom on the other hand doesn’t understand why I wear an “old rag” among the otherwise nicer things in my closet that aren’t on their last legs.

  • Danielle Cardona Graff

    And I love this btw! There’s nothing I love more that a good story behind an awesome article of clothing or accessory.

  • T-Fierce

    Well now I have a deep, deep desire to match my socks to my hats!!!

    • Haley Nahman


  • ashley

    This is my favorite article of all time. ESP because just finished Kondo-ing and won’t be buying a single new thing all of 2018 👊🏼

    • ashley

      also jayna is so effing cute

    • oh wow that is a serious statement if I’ve ever heard one! how do you plan on sticking to it? (not to rain on your plans but I’d have so much trouble)

      • ashley

        might be plotting a pair of jeans and a dress coat before dec 31 hits. But just realized have a version of everythingishop or look for. Even catching myself looking to recreate or replace things once donated or tossed in the past. The madness must stop

        • I applaud you! if you don’t mind me asking, what’s your go-to? do you wear more jeans or skirts? what about shirts/cardigans/jackets? I’m a student/parttime retail worker and my closet is a jumble of things I all like but it’s all different styles and stuff

          • ashley

            Hi there! Mostly jeans cords pants. Skirt rarely for a dinner nye wedding etc. mine was a jumble of styles but I️ had to finally get real about what I️ feel most comfortable in / which leads to what I️ wear most often

          • cords as in corduroys?
            oh that is my problem too, my closet/tastes are very eclectic so not everything goes together. to make things weirder, I also work in fashion and have zero problems putting together outfits for others lol

  • tmm16

    Swooning over Juliana’s look but tbh I love them all

  • Ma

    I have two sets of Nike pants+tshirts which I bought when I was 11 – I haven’t grown much since, but have put on about 30 pounds (as it should be), and they still, loyally, fit me. Other than that, I have a Diesel denim jacket which I bought when I was 13 and have worn almost every weekend since. I can assure you nothing I’ve bought since seems to hold up quite as well as these…

    I’m impressed by the fashionable choices above though – everything seems like stuff I would buy right now (maybe not the Chanel boots haha)

  • pwatt err s

    My dad gave my mom a dark red short waisted leather jacket for their first anniversary, and she gave it to me. It’s two years older than I am, so it’s 60 and perfectly worn in all the right places. When I wear it I feel cool, and chic in an individualistic sort of way.

    • Shivani Lakshmi

      wow!! that’s so incredible & lovely.

  • JennyWren

    Sadly, I have yo-yoed sizes so many times over the last decade that I don’t have much in my warderobe older than three years. I have a whole vacuum pack bag of clothes is sizes I’m currently not, though! I do have a vintage fur jacket I got when I was working in a charity shop (the UK edition of a thrift store) back when I was 21; the shop couldn’t sell it so I put five pounds (about $7) in the till and saved it from the bin. Ten years on I never wear because it I’m undecided about the politics, but I do love to put it on and touch it.

  • Bailey Stark

    Im almost 20 and I still have shoes that fit me when I was 12. LOL

  • bananarama

    I live in my mom’s old Levi’s 501s from the 70’s… somehow, they fit me perfectly and make me feel like the absolute most badass version of myself! also, I have a vintage 1940s beaded clutch that was my late grandmother’s, and I love it bc a) it’s super cool and b) it makes me feel connected to her 🙂

  • Mary

    I still wear my long-sleeve, forest green, double u-neck dress from American Apparel. I’ve had it for 9 years! I mean, yes, I have a host of vintage t-shirts and denim jackets that I inherited from my mom & dad that are older than I am, but as far as things that *I* bought for myself and have kept- this dress reigns. I cut it into a shirt and probably only wear it 2-3 times a year now, but still!

  • mapillski

    Man, I can stretch out the life of a t-shirt. I have the jersey from my 4th grade rec soccer team still in my drawer and still wear it in the summer. Since I was a teen in the mid-aughts, thankfully all of my favorite clothes from middle school and high school were truly too hideous to be seen outside of an embarrassing throwback Thursday photo and have all been sent to Goodwill. I still have my junior prom dress in my closet though, because wearing it was the prettiest I have ever felt.

  • eva

    this piece really SPEAKS to me!! 20% of my wardrobe is 20 or more years old. i wear handmedown pieces that belongs to my MOM and GRANDMOTHER in their 20s. some stuff is just timeless and quality of material and craft was so much better then! i have a chloe blazer from the 70’s and a silk dress my mom made in 1972 for a NYE party. the oldest pieces that came into my life as “mine” first are a teal blue t-shirt from the monterey bay aquarium i got aged 10 [albeit now it’s a cut-off tank] and a pair of paisley docs from 1994. i wouldn’t go so far as to call myself a clothing hoarder but i had such strong purge regrets and have been around the trend carousel enough times to recognize what’ll cycle back.

  • Hannah

    I love Yaminah’s advice about white-on-white. It’s true. I had a white rental car one day and wore white-on-white, white shoes even. I wasn’t trying to intentionally match the car I don’t think but I rolled up to a coffee shop and a guy said, “Did you just really drive up in all white in a white car?” and I paused for a second before answering, “Sure did, chief.” or something to that effect. You have to own it and I think that makes it powerful. Also, very hard not to get dirty, takes a lot of effort and attention. Fun piece all around 🙂

  • Rosemary

    This is my new fave MR article

  • Calla

    I spent most of the Melbourne winter stomping around in the jodhpur boots I got when I was 14. They were the most expensive boots I’d ever owned and a mark that my feet had finally stopped growing. Because I actually rode in them they have worn beautifully, with the neck stretched out, and been re-soled twice. Realised while stomping around a leech-filled forest last month that they have gaping holes in the side, but I still can’t give them up.

    I have a new, much more expensive pair of jodhpur boots now but I know they just won’t wear the same way because I don’t ride anymore.

  • ladle

    I would be a champion at this. I have things I wore in middle school that I wear now. I have things my mom wore in the 70s, and my grandma wore in the 60s and 50s. I would have more of them if I didn’t get taller and went up a shoe size – mom has these awesome shoes she was saving for me that she used to wear when she was in her 20s and all cool. They all look new because if there is one thing I know is how to wear something till it falls apart in my hands. I almost cried when I had to get rid of the best jeans I ever owned, because they didn’t fit me anymore.
    The bad thing is that I can be such a cheapskate and refuse to buy new stuff, unless I have nothing to wear. 😀

  • rachel

    The oldest item in my closet is my grandma’s leopard fur jacket, but the item thats been in my closet the longest is much simpler: two long sleeve Pendleton dresses made from thick organic cotton that my mom bought me c. 1997. Then, they were loose comfy near maxi dresses (I was 6), now they are fitted, knee length, and perfect for work. Thanks Mom!

  • Lyndsay

    I’ll have had my leather moto jacket for 17 years later this month – half of my life! I remember the day i bought it because it was my high school bf’s birthday ❤️ It’s made of really thick leather that was honestly too stiff and weird looking for the first 10 years or so, but it looks sick now that it’s suitably bashed and worn in.

  • vss

    Love, love, love this article.

  • I was surprised at the fact that each piece, though old, still look AMAZING! I, being only 16, have a piece that is 6 years old, which is my “oldest”—I didn’t realize that was quite young as some of the people interviewed had pieces over 10 YEARS OLD!! XD
    It was exciting seeing older pieces put together as well to all together make a cute look! So refreshing!

  • interview with Juliana Salazar 🙋🏽🙋🏽🙋🏽🙋🏽🙋🏽🙋🏽🙋🏽🙋🏽🙋🏽🙋🏽🙋🏽🙋🏽🙋🏽🙋🏽🙋🏽

  • Emma

    da boots<3

  • Sophia F.

    What an awesome piece! I’m amazed though at how long people have saved things. I got rid of all my too small clothing as I grew out of it in middle and high school – even shirts because my chest grew far, far bigger than the rest of me. Now, at 31 and post-kids, I’m actually smaller than I was when I headed to college, and have half the boobs – I could totally fit in some of my awesome things from middle school if I hadn’t given them away ages and ages ago, and can’t wear things from five to ten years ago because they’re too big.

  • Lynda Langlois

    gorgeous Jaime classic saves for sure!

  • Allegra

    ugh i had the most amazing oversized blue men’s XL cotton henly that my dad got for free while shooting a Dockers commercial and I used to wear it tucked in to high waisted jeans with black high top converse and a side braid. i was hot shit.

  • Charlie

    I still wear a hair pin that my dad bought me after a horrible haircut when I was 6. I’m 26 now!

  • The absolute oldest thing I own is a fur stole from the 1940s that I inherited this year, and love wearing all the time. The thing that’s been in my possession the longest is an Elizabeth Arden graphic tee my mum had in the 80s that I stole as a five or six year old aka 22 years ago, and I still wear it with trousers, jeans, or a pencil skirt under a blazer.

  • Basil

    The oldest thing I have is a gold lame bag that was my grandmother’s. I got it when I was looking for an evening bag to use at my brother’s wedding (I was a bridesmaid and the dress was gold). I couldn’t find anything, and then my mom gave me the bag, which granny had bought for my uncle’s wedding. First of all, I didn’t realise granny had such pizzazzy taste, and secondly it’s so versatile, it goes with everything. I love that bag