It started as a tipsy dare at Emma’s birthday dinner. Six of us were crammed into a booth at this dimly lit restaurant in Williamsburg, halfway through our second round of natural wine, when the conversation turned—as it inevitably does in a group of fashion people—to the outfits in the new Challengers movie. This somehow spiraled into a heated debate about the greatest fashion moments in film history, with everyone talking over each other to defend their picks. Penny was ride-or-die for Diane Keaton’s Annie Hall looks. Tara wouldn’t shut up about Zendaya’s entire filmography. Devon, the vintage dealer among us, kept bringing up obscure Italian films from the ’60s that none of us had seen.
“You know what,” I said, cutting through the chaos after my third glass of something orange and funky-tasting, “I could recreate any iconic movie look with just thrift store finds. Any of them.”
The table went momentarily silent—the kind of silence that immediately makes you regret opening your mouth.
“Even Cher’s yellow plaid outfit from Clueless?” challenged Tara, who knows my complicated relationship with anything yellow.
“Especially that one,” I replied, with the unearned confidence that only comes from natural wine and an audience.
“Ooooh, we need to document this,” Emma squealed, already reaching for her phone. “Harper’s Thrift Store Movie Challenge!” By dessert, we’d created a spreadsheet with movie outfit assignments, deadlines, and a scoring system that made sense only in that moment and would prove completely unusable later.
The next morning, I woke up to 37 notifications from our group chat and the sinking realization that I’d committed to a project that would consume my weekends for the foreseeable future. Typical. This wasn’t even the most ridiculous thing I’d agreed to after wine—that honour belongs to the time I volunteered to hand-embroider napkins for Penny’s wedding, having never embroidered anything in my life. (She ended up with cocktail napkins that looked like they’d been stabbed repeatedly by an angry child, but that’s a story for another day.)
But I’m not one to back down from a fashion challenge, especially one involving thrift stores. As someone who grew up dumpster-diving at Brooklyn vintage shops and convincing my mom that yes, I absolutely needed that hideous ’80s prom dress “for creative purposes,” I was born for this. Plus, it seemed like the perfect opportunity to prove that you don’t need to drop serious cash on fast fashion knockoffs when the original inspirations are probably hanging on a rack at Goodwill right now.
I decided to tackle six iconic movie looks over six weekends, giving myself a $50 budget per outfit and limiting my hunting grounds to thrift stores, consignment shops, and the occasional church basement sale. No Etsy, no eBay, no Instagram vintage sellers—just good old-fashioned physical thrifting, fueled by patience and hand sanitizer.
First up: the aforementioned Cher Horowitz yellow plaid ensemble from Clueless. I’ve always had a complicated relationship with this outfit, mostly because: a) yellow washes me out completely, making me look like I’m recovering from some Victorian-era illness, and b) the knee socks awakened something in too many men my freshman year of college when I wore them for Halloween. But I had to start with a challenge, so yellow plaid it was.
I hit the Goodwill in Park Slope first, where I immediately struck gold with a yellow plaid skirt that was more muted than Cher’s sunshine version—more dijon than French’s, if we’re being specific about our mustards. It wasn’t pleated, but the A-line shape still worked. Eight dollars. For the matching jacket, I came up empty at three different stores before finding a women’s yellow blazer at Housing Works that was plain, not plaid. Thirteen dollars. Not perfect, but I could work with it.
The stroke of genius came when I found a child’s yellow plaid backpack at a church thrift shop for $3. I sacrificed the poor backpack, cutting it apart and using the fabric to create appliqué patches for the blazer lapels and pockets. The knee socks were easy—$2 at a discount store. White button-up from my own closet. I already owned a similar-ish pair of Mary Janes from a previous Alexa Chung style phase. Total damage: $26, plus the ethical weight of destroying a perfectly good child’s backpack.
The final result was… not bad, actually? More “college theatre major’s interpretation of Cher Horowitz for a scene study” than exact replica, but recognizable enough that three separate people yelled “As if!” at me when I wore it to brunch. Emma documented the entire look for Instagram, where it racked up enough likes to convince me this project wasn’t completely ridiculous after all.
Encouraged by my moderate success, I moved on to something more challenging: Penny Lane’s shearling coat and tiny sunglasses from Almost Famous. This was Devon’s suggestion—she’s been trying to get me to buy a shearling coat from her vintage shop for years. The coat was going to be the make-or-break piece here, and I’m not going to lie, I was worried. Real shearling, even thrifted, usually blows past my entire $50 budget.
I spent two entire Saturdays hitting every thrift store in a 15-mile radius. Nothing. I was about to admit defeat when I remembered this weird warehouse thrift shop way out in Queens that my ex-boyfriend had taken me to years ago. It was the kind of place where you need tetanus shots before and after visiting—just mountains of unsorted clothes where everything costs $5 regardless of whether it’s a Hanes t-shirt or a designer piece someone donated by mistake.
Three hours of digging later, covered in dust and questioning all my life choices, I found it—a tan suede coat with matted faux shearling lining that had definitely seen better decades. It smelled faintly of mothballs and someone’s grandpa’s cologne, but it had the silhouette I needed. Five dollars. I took it to my neighborhood dry cleaner, who looked at me like I’d brought in a dead animal when I asked if they could clean it. Forty dollars later (breaking my budget, but necessary for health reasons), the coat was transformed.
The rest came together easily: flared jeans from Beacon’s Closet ($12), a cropped band t-shirt from a bin sale ($3), and tiny oval sunglasses from a street vendor who was definitely selling counterfeit everything ($5). I borrowed Devon’s crochet bag to complete the look. We shot the photos in Prospect Park at sunset, and I have to say, I felt like I should be following a 1970s rock band on tour. Several dog walkers gave me concerned looks, probably wondering why someone was dressed for winter in 75-degree weather.
My third challenge was Audrey Hepburn’s black Givenchy dress from Breakfast at Tiffany’s. Classic, seemingly simple, but potentially a nightmare to find in the right cut. After striking out at my usual spots, I decided to try the thrift stores in the Upper East Side, figuring rich ladies might donate better black dresses. Smart move. At a consignment shop on 86th Street, I found a simple black sheath dress that had the right neckline, if not the exact back cutout of the original. Fifteen dollars, which seemed like robbery considering the “dry clean only” label from a brand I recognised from the fancy department stores I pretend I don’t shop at.
The pearls were trickier—good fakes don’t usually end up in thrift stores. I compromised with a $7 multilayer pearl necklace from a charity shop that benefited stray cats (or maybe children with cancer—the sign was confusing and I was too embarrassed to ask). Sunglasses came from the same probably-illegal vendor as the Penny Lane glasses. Five dollars. Black gloves from a vintage store’s sale bin, marked down because of a small tear at the wrist. Eight dollars. Tiara… well, I cheated slightly and borrowed a rhinestone headband from Emma’s extensive collection of “things I bought for themed parties and never wore again.”
We shot the photos at 5 AM on a Sunday outside the actual Tiffany’s on Fifth Avenue, much to the confusion of early morning security guards and a group of stumbling club-goers who were still out from the night before. One of them recognised what we were doing and insisted on taking photos with me, which is how I ended up with a series of blurry pictures where I’m trying to channel Audrey Hepburn’s elegance while being hugged by a woman in a torn sequin dress who kept yelling “HOLLY GOLIGHTLY IS MY SPIRIT ANIMAL!”
For my fourth challenge, I tackled something more contemporary: Margot Robbie’s pink gingham outfit from the Barbie movie, which had been absolutely inescapable on social media. The dress was surprisingly easy—I found a pink and white checked sundress at a church basement sale in Bed-Stuy for $6. It wasn’t as structured as Margot’s, but the pattern was spot-on. White cat-eye sunglasses from a vintage shop’s accessories bowl. Three dollars. White headband, also from my own collection of “things I bought and wore exactly once.”
The pink mules were the sticking point. After searching everywhere, I finally found a pair of white heeled sandals at Goodwill ($10) and spent an evening painting them pink with fabric paint I already owned from a previous DIY disaster. They looked… homemade, to put it kindly. Like something a five-year-old would create for a school project. But from a distance, in photographs, with the right filter? Passable.
I wore the full look to the farmer’s market, where a group of tween girls followed me around not-so-subtly taking pictures and whispering. I couldn’t tell if they thought I was doing an impressive Barbie cosplay or if they were quietly mocking the weird adult woman dressed like a doll buying heirloom tomatoes. Possibly both.
My fifth recreation ventured into riskier territory: Mia Wallace’s iconic white button-down and black pants from Pulp Fiction. This sounds simple but finding the right oversized white shirt with the correct collar shape proved surprisingly difficult. I eventually found one in the men’s section at a Salvation Army for $4. The black straight-leg pants came from a consignment store in Bushwick for $18. Black ballet flats from my own closet (who doesn’t own black ballet flats?). The short black bob wig was where I had to get creative.
After determining that even the cheapest Halloween wigs would blow my remaining budget, I reached out to Tara, who’s worked as a stylist on photo shoots and keeps a stash of random accessories in her apartment. She let me borrow a black bob wig that she swore had been properly cleaned since its last use, though she wouldn’t tell me what that use was, which was mildly concerning.
We recreated the famous dance scene in my living room, with David, my neighbour who I barely know but who was very eager to help once I mentioned Pulp Fiction, stepping in as John Travolta. The photos turned out better than expected, though we both drew the line at mimicking the heroin overdose scene. Some things just don’t need to be recreated for Instagram.
For my final challenge, I decided to go for something that felt personal—Diane Keaton’s quirky menswear looks from Annie Hall, which had been Penny’s original suggestion. This was actually the easiest outfit to thrift because—secret confession—it’s not far from how I dress on weekends anyway. Wide-leg khaki pants from a vintage shop in Greenpoint ($14), oversized men’s vest from a charity shop in Chelsea ($7), white button-down from the same Salvation Army as the Pulp Fiction shirt ($4), and a tie from a bin marked “$1 each or 7 for $5,” which is the kind of nonsensical pricing that makes thrift shopping both frustrating and magical.
The hat was the final touch—not exactly like the one in the movie, but a worn-in brown fedora that I found at the bottom of a box of Halloween costumes at Goodwill. Three dollars, and worth every penny for the perfect slightly-crushed look that gave it character. The whole outfit came together for $29, making it my second cheapest recreation after the Cher look.
We shot the photos in Central Park, with me leaning awkwardly against trees and trying to capture Diane Keaton’s specific brand of neurotic charm, which mostly resulted in pictures where I look like I really need to use the bathroom but am trying to play it cool.
Looking back at all six recreations, I’m struck by how possible it was to capture the essence of these iconic outfits without spending a fortune or contributing to fast fashion. Were they exact replicas? Absolutely not. Did they have loose threads, mysterious stains I chose to ignore, and previous lives I tried not to think about too hard? You bet. But they had something that mass-produced “inspired by” pieces lack—character, sustainability, and the satisfaction of the hunt.
The entire project cost me less than $200 (excluding the emergency dry cleaning for the Almost Famous coat, which I’m filing under “health expense” rather than “fashion budget”), countless hours digging through bins and racks, three minor allergic reactions to unknown substances on vintage clothing, and one very confused Uber driver who picked me up while I was in full Barbie mode and seemed genuinely concerned that a life-sized doll had ordered a car.
Was it worth it? For the stories alone, absolutely. For proving my wine-fueled boast to my friends, definitely. But mostly for the reminder that fashion’s most memorable moments aren’t about having the exact designer piece or the perfect replica—they’re about capturing a feeling, a character, a time.
And sometimes, the most interesting version of an iconic look is the one that’s filtered through your own resourcefulness, creativity, and willingness to dig through a bin of strangers’ discarded clothes while holding your breath.
Emma has since suggested we tackle music video looks next. I’ve told her I need at least a month to recover before I’m ready to hunt for a conical bra to recreate Madonna’s Blonde Ambition tour. Some thrifting challenges require special mental preparation—and possibly another night of natural wine to agree to them in the first place.
