I Asked 5 Women to Find and Wear the Oldest Thing They Own
12.01.17

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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