I Can't Stop Buying Back My Childhood Wardrobe

From Dooney & Bourke to dELiA*s, these old favorites bring me joy. I basically had to find them and buy them again.

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I Can't Stop Buying Back My Childhood Wardrobe
Photo: Samantha Sutton/InStyle

Like many millennials, I desperately miss the carefree days of my childhood. I often wish I could travel back in time and relive specific '00s experiences, like playing Snake on a Nokia cell phone, or putting Ashanti lyrics as my AIM away message while watching Smallville.

Perhaps my tendency to get nostalgic is why I've embraced Y2K fashion with open arms. I'm finally wearing items like the intense platforms and leather blazers I was too young for the first time around. Plus, with the resurgence of so many old trends, I've felt inspired to buy back pieces I actually used to own, too.

It's a spiral that started out with a beige, monogrammed Coach purse. Seeing so many baguette bags on the arms of models, while reflecting on my first major fashion purchase, made me wonder where the heck my favorite middle school staple was buried. Wouldn't it be funny if I rewore that exact purse, giving the trend a personal twist instead of shelling out money on a modern-day copycat? But when I couldn't find my own version in storage, I decided to buy a $40 alternative on Depop — and ultimately discovered a treasure trove of throwback items.

I Can't Stop Buying Back My Childhood Wardrobe
Samantha Sutton

Once I had that Coach purse in my possession, I thought about Dooney & Bourke, another brand I loved in the early '00s. I had spend my tween years lusting after a bag from its heart-printed collection — something you can now buy for about $30 secondhand. So, once again, I added another throwback to cart.

And from there, I simply couldn't stop.

However, I wasn't just coming up with the rebuying ideas on my own; I was influenced by celebrities, too. When Olivia Rodrigo wore a vintage Betsey Johnson dress to an event earlier this year, I went on a hunt for a ruched number I should have worn to my prom. It eventually led me down a dELiA*s rabbit hole, not only in search of vintage butterfly-prints — very '00s and very Dua Lipa! — but also graphic T-shirts. I always regretted giving away a quirky, green, gumball top I had throughout high school. With the return of the more extreme Ed Hardy designs, I decided needed it back now, and I eventually found it on Poshmark for $5.

I Can't Stop Buying Back My Childhood Wardrobe
Samantha Sutton

Even before this phase of my life, I had become addicted to buying clothes that really brought me joy. But unlike poufy dresses and sequins, these pieces also came with the priceless addition of happy memories — even if they weren't my original version. Pulling on a shirt I loved when I was a freshman in high school just reminded me of a simpler time. Back when I hung out at the mall every Friday night, or "stressed" over what time we were seeing Mean Girls at the movies.

There's also the fact that even as I shop for my old favorites, I still feel very on-trend. Resale site Rebag has hard data that at least backs up my love of '00s bags, proving that many millennials are on this same path down memory lane.

"Some of us remember being in our teens and twenties and lusting after specific luxury items, like the Balenciaga City or Fendi Baguette, but not having enough disposable income to afford those things. Millennials were aged 4 to 19 in 2000, and 14 to 29 when the decade ended," explains Charles Gorra, the company's founder and CEO. "Now, thanks to resale platforms like Rebag, Millennials — who are also often called the Nostalgia Generation due to their predilection for things like #flashbackfriday and #tbt — can go back and find the now-vintage items or their newer re-editions and purchase them."

According to Rebag's 2021 Clair Report, there has been a "significant boost" in searches for '00s favorites, like the Lady Dior — which was once spotted on Gossip Girl — and the Fendi Baguette, which was popular due to Sex and the City.

Personally, I've been seeing a lot of multi-colored Louis Vuitton pochettes popping up on the streets of Brooklyn — and, yeah, felt an urge to add it to my collection, too.

Still, the best part about buying back my old childhood wardrobe isn't the fact that it feels cool or on-trend to do so. These pieces don't need to be luxury or earn someone's stamp of approval for me want them. I'm re-wearing my old clothes and accessories for personal reasons. Much like all those 30-something memes and '00s reenactments on TikTok, they just bring a smile to my face. They may spark a conversation with an old friend, or a stranger who similarly remembers poring over their dELiA*s catalog or hanging out at the mall, and stuff like that just makes me happy. It's as simple as that.

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