I Thought I Was an Expert Thrifter. Then I Went to an Estate Sale.

I Thought I Was an Expert Thrifter. Then I Went to an Estate Sale.

My sophomore year of college, my grandfather, who I was very close to, passed away. In the wake of his death, my grandmother gave me piles of his clothing—patterned sweaters and knit cardigans, cloth handkerchiefs and playful ties, all of which he’d kept in impeccable condition. These pieces became a channel through which to keep his memory alive. In all my years of secondhand shopping, I’d never found that sense of emotion or connection in any of the clothing that I thrifted. That is, until I visited my first estate sale.

This past January, a friend posted a story on Instagram detailing a large estate sale taking place in the historic district of Prospect Lefferts Gardens. From within the five-story Brooklyn home, she showed off furniture, art, jewelry, and lots and lots of elaborate hats. Just text this number for the address, she instructed. My interest was piqued.

Joel Calfee

A view from the historic street where the house was nestled in Prospect Lefferts Gardens.

With three friends in tow, I ended up at the house of “Auntie Evelyn,” a woman whose rich life could be seen not only in her things, but in the family that filled her halls. Young children ate pizza downstairs and Evelyn’s sister told stories from the living room couch. I learned of her career in medicine, her years spent traveling, and the lively parties she and her husband had thrown in their speakeasy-like basement. And by the end of the day, I went home with a trench coat, a suit set, a lacy cape, vintage Spanish boots, and more that had belonged to her—all for less than $100.

inside view of the home

Joel Calfee

An inside view of Auntie Evelyn’s home.

As soon as I left, I felt myself itching to visit another estate sale, so I went online to see if other people my age were tapping into this singular thrifting experience. Estate sale shopping may sound like an activity for retirees, but as it turns out, interest is growing, especially amongst Gen Z. Look up the hashtag #estatesale on TikTok, and you’ll find over 80k videos of shoppers showing off their hauls or documenting their experiences. Search the same term on Instagram and you’ll find 580k+ posts of the same kind, with #estatesalefinds itself having 500k uploads.

It makes sense that Gen Z would love them—we’re a generation that romanticizes vintage by collecting vinyls and using film cameras, and we’re also highly attuned to sustainability. As the algorithm continues trying to feed us mass-produced fast fashion to appease every trend, we continue finding new ways to upcycle (especially if it fits our twentysomething budgets).

I realized how much these sales appeal to my generation when I took in the other visitors at Evelyn’s house. It was almost entirely a crowd of younger women. Nobody seemed to have known the owner or her family beforehand. Quickly, we transformed the second floor into one giant dressing room, as tiny groups huddled over boxes, chests, and drawers. We tried things on over our clothes and encouraged each other to buy them like a friend group straight out of a 2000s rom-com. It was a sense of community I rarely find when shopping, and the clothes were a type of quality I rarely find, either.

At first, it felt strange to be parsing through the things of someone I didn’t know. But then I realized each visitor was carrying on pieces of Evelyn’s memory, be it through one of her vintage samba records or one of her pairs of lavender heels.


“When it comes to shopping secondhand, I definitely think the highest quality items come from estate sales,” says Natalie Joy, a sustainable jewelry designer and self-described “avid thrifter.”

Estate sales are especially good for nabbing super-rare finds. No one knows this better than Joy, who went viral in 2023 when she shared a TikTok recounting the moment she unearthed a quilted jacket from Ralph Lauren at an estate sale. Initially drawn to the unique material, Joy bought the piece for a mere $10, only to find out it hailed from a Fall 1982 collection where Lauren used pieces of antique quilts as a way to pay tribute to American folk art. Currently, one of the only surviving pieces lives in the Goldstein Museum of Design in Minnesota. Joy found hers in a box.

“Most people don’t want to dig that hard, so you can find some really special things if you have the patience,” she says. “I found the rare Ralph Lauren sweater in a cardboard box underneath a folding table with sheets and tablecloths piled on top.”

Macy Eleni, the social media “thrifting queen” and author of Second Chances: The Ultimate Guide to Thrifting, Sustainable Style, and Expressing Your Most Authentic Self, also emphasizes that estate sales can be the right place to find a designer gem. “Truly most of my favorite wardrobe pieces have come from the old homes of LA icons passed,” she says. “A few faves are my Gucci Jackie bag, Moschino bikini, Halston dress, Balenciaga Le City long wallet, and a white tracksuit (which belonged to the late great Alex Trebek)!”

Of course, you’re more likely to find something luxe if you’re hitting sales in Los Angeles or New York, but Evan Owens—a filmmaker and one of the operators of Alabama Estate Sales—has seen similar discoveries from within her rural business in Alabama. She recalls moments where her team found never-before-seen photos of Ernest Hemingway and signed proofs from Salvador Dalí. “That was amazing,” she says.

Because these sales can offer high-quality pieces for cheap, they’re also a good way for young people to get on their feet. From an organizational side, Owens has certainly noticed a surge in Gen Z interest. “We definitely get a lot of first-timers,” she says. “A definite increase in the younger crowd, and there’s a lot of younger couples that come through that are moving in together and, you know, just buying new furniture or small stuff, like decorative items. It’s good to see.”

Owens sees people come far and wide to Alabama, from neighboring states like Mississippi, Louisiana, and Tennessee. Social media is partly to thank for the increased visibility, but so are websites like estatesales.net, which round up everything from auctions to business closings, and conveniently organize them by location.

Eleni found an audience when she began documenting her estate sale adventures five years ago. “I started posting my estate sale vlogs on TikTok back in 2020 and since then it’s been wild to watch it become more of a normal way to shop,” Eleni says. But depending on where you go, you may need to approach the sale with a bit of patience.

“My tips for someone attending their first estate sale would be to not let the frenzy of it all deter you,” Joy notes. “I rarely go on the morning of day one because the lines are too stressful for me. I recommend going on the afternoon of the first day, when the getting is still good, or on Sunday when everything is 50% off.”

outfit photo

Joel Calfee

Modeling a vintage pair of Spanish boots I found at the estate sale.

Eleni adds, “It can be more competitive in the moment. Thrifting is usually a lot more leisurely (unless you’re at the bins)—you get to sift the racks at your own pace versus being in one closet with a bunch of other people searching at the same time.”

And if the family is there, it might feel meaningful to connect with them about the stories of their loved ones, like I did. But Owens warns that these matters can be delicate. “With our company, we don’t allow the family to be there for the reason being, it’s really hard to see strangers rummaging through your life and haggling over, you know, your great-grandmother’s tablecloth,” she points out.

It certainly makes sense when you consider the emotional nature of the whole affair, but for me, the sentimentality was the highlight. I think, as questions around where our purchases come from become more pressing, options like estate sales will be an increasingly appealing option.

It’s likely only a matter of time before estate sales become trendy, too. A little media exposure goes a long way—think of what The Queen’s Gambit did for chess or Stranger Things did for Dungeons & Dragons. Owens is actually using her firsthand experience to create a sitcom centered around the characters that show up to these sales.

“It’s based on me and my mom and our crew that we work with,” Owens reveals, noting that the show is currently in production and it will feature stars like Outer Banks’s Chelle Ramons and viral internet star Andi Marie Tillman. “We’ve had some pretty hilarious and crazy things go down, so I was like, ‘People need to know about this niche group that come to estate sales.’” (Her experiences involve run-ins with a chronic bathroom user and a kitchen pyromaniac, but I’ll save the details for the series release.)

Along with the zanier stories, though, Owens emphasizes the idea that estate sales can be a place for community and connection. “We’ve made some of our best friends through estate sales,” she says.

Eleni agrees, adding, “It’s always a more positive experience for everyone when people are just kind and courteous of each other. Good vibes bring the good finds.”

outfit photo

Joel Calfee

More finds from Auntie Evelyn’s fabulous wardrobe, including a green silk set and lavender heels.

It’s not necessarily about scoring great items every time, either. Joy notes, “What I love most about thrifting is the hunt. Oftentimes, you’ll walk away with nothing, and that’s just part of it. It’s even more rewarding when you do find something special because you had to work for it! It’s a great practice in developing your own unique taste.”

After my estate sale visit, I found myself wearing my new clothes to work and out with my friends. Every time, someone would compliment my outfit and then ask where I found it. And every time, I’d smile and start to explain, “Well, these were Evelyn’s…”



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