Warning: spoilers for Freakier Friday below.
The press tour for Freakier Friday — the sequel to 2003’s Freaky Friday starring Lindsay Lohan and Jamie Lee Curtis — has been a parade of Easter egg-heavy looks (like Lohan’s lavender gown and red guitar purse), prepping us for the movie’s bound-to-be-iconic costumes. I just couldn’t have prepared myself for all the luxury fashion I’d see on screen.
It’s been 22 years since Anna (Lohan) and Tess Coleman (Curtis) switched bodies — giving us a classic makeover montage and many enviable looks — and now the mother and daughter are returning to cinemas on August 8, for what’s amping up to be another fashion spectacle.
“I feel like it was conversations with [director]Nisha [Ganatra] and with Jamie and Lohan — just to see where they thought their characters were going to be and what they would look like,” Freakier Friday costume designer, Natalie O’Brien, tells Refinery29. “I’m a sucker for nostalgia, so we wanted to pay homage to what they had already done and not steer too far from it. But we also don’t want to hit you over the head with what you’ve seen already.”
This time, in a freakier twist, Anna — who’s planning to marry single dad Eric (Manny Jacinto) — swaps bodies with her 15-year-old daughter Harper (Julia Butters), whose tomboy surfer aesthetic centers on her signature beanie and overalls. Meanwhile, Tess swaps with her soon-to-be-granddaughter, Lily (Sophia Hammons), a preppy, aspiring designer who sticks to thick headbands, bows (peep the Coachtopia bow bag!), and lots of Vivienne Westwood. (She looks like your typical Disney Channel fashionista.) This all results in four characters comically stepping into each other’s shoes (many of which are Jimmy Choo!), producing even more iconic looks than the original movie.
After leaving her band Pink Slip to raise Harper, Anna is now working as a musician’s manager at Capitol Records. “She’s a cool mom. She didn’t fall off and lose her rocker sense,” says O’Brien, adding that she took inspiration from actress and singer Charlotte Gainsbourg’s effortlessly chic and timeless look. “[Anna] still stayed in the music industry, so I think that’s important to showcase that with her clothes. I liked the idea of an old leather belt that she’s had for a while and some star-studded boots that aren’t corny and kind of cool for her everyday look.”
Anna’s success in the industry also explains the luxury pieces she’s accumulated in her closet. From Olivia Von Halle silk pajamas and (not one, but two) Self-Portrait bedazzled dresses to cool-girl looks (i.e. a Staud dolphin dress, The Frankie Shop suit, and Dôen floral dress), her style is brighter, sparklier, and fancier than her grungy teenage aesthetic.
“I also feel like the only way I can get Lohan in a rash guard, has to be like a Balenciaga [version]—something sick — and it worked,” O’Brien shares, referencing the palm tree and sunset print top Anna wears after swapping bodies with Harper. The surfwear looks continue with Anna (as Harper) later stepping out in a charming floral Cynthia Rowley wetsuit.
Meanwhile, Tess is still a successful psychiatrist and author, but has also added podcaster to her repertoire. While in Freaky Friday she wore lots of all-black outfits, her style has slightly evolved into monochromatic “groufits” (along with mauve, burgundy, and navy) with colorful pops from the silk scarves tied around her neck. However, her style is anything but matronly — I spotted her wearing the exact Reformation cardigan I own, to which O’Brien exclaimed: “Oh my God! Jamie loves Reformation.” But Tess’ most exciting looks come after the swap — prompting O’Brien to reassure Curtis: “It’s good that you feel uncomfortable because you’re playing a 15-year-old teenager, right?”.
Like in the first movie, the characters switch bodies overnight while sleeping in the same house. Because they each wake up in a different body, their pajamas stand out as key looks — and visual clues for the audience.
“I liked the idea of having the matching sets for everybody just to kind of feel like they’re adults, especially for Tess and Anna,” O’Brien shares, having dressed Anna in an Olivia von Halle set, complete with a pink cloud print with crystal buttons, and Tess in a royal blue set with a lacy negligee peeking from underneath. Harper’s Urban Outfitters sweatsuit is slightly mismatched to reflect her unfussy style, while Lily wears a frilly Petite Plume short set. “I loved that Lily stood out […] I didn’t want to do the nightdress like they had done in the past. So I was like, let’s make it different.”
As the characters deal with their new reality — and what they’ll wear to take on the day — Anna (as Harper) and Tess (as Lily) have a mini makeover to revamp the mothers’ clothes to be more youthful. (This is where Anna’s Balenciaga rash guard comes in, paired with trendy jorts, a blazer, and Adidas sneakers.)
Speaking on Tess’ light-blue Reiss suit (seen in the movie poster), O’Brien says: “It was written in the script that she cuts her hair. And I’m like, if she has scissors, let’s cut the blazer and trim it. Let’s make it a little bit more Vivienne Westwood fashion, grungy, pop punk. I think it makes more sense since Lily is a fashion designer.” The finishing touches of her blazer-turned-vest look? A Jean Paul Gautier printed mesh top and chunky New Balance sneakers.
“I love their outfits when they’re coming down the stairs. To me, it made a mark on me from the first movie. It felt an authentic representation of the two of them,” says O’Brien, about the duo revealing their post-makeover looks for Harper (as Anna) and Lily (as Tess). “Having to explain to the audience that that’s not who you think it is and now we’re switching with four people is complicated. We have to give as many clues and identities as possible.”
When Anna and Tess attend a Rolling Stone photoshoot for Anna’s client, Ella (Maitreyi Ramakrishnan), we get another mini fashion show as they wind up joining the shoot and trying on several elaborate outfits. These include food-themed looks for Ella’s album entitled Hungry and red-carpet-ready ensembles that they then wear out on the town.
From the racks, Anna pulls a Christopher John Rogers red bustier top and army green handkerchief skirt, paired with pink Dior sunglasses, a rosette choker, and black mesh Norma Kamali gloves (all pictured in the poster). O’Brien says this pays homage to the character’s infamous Freaky Friday outfit: a black-and-red baseball tee, khaki cargo pants, and guitar pick choker. While it’s totally extravagant, it’s exactly what I want from a Disney movie look.
Meanwhile my favorite look for Tess is a denim Cinq à Sept drop-shoulder jacket (covered with tons of large safety pins) and matching denim trousers with a black Max Mara bustier belt. She’s also styled to the nines with some of O’Brien’s favorite accessories in the movie: a Coperni emoji OK earring, Ariana Boussard bracelet cuffs, and a Simon Miller silver puffy heart-shaped purse. It’s the perfect blend of Tess’ go-to monochromatic style and Lily’s fashion-forward touch.
Even more clever styling details come out during post-swap scenes including the pickleball tournament, wedding rehearsal lunch, wedding day, and a surprise Pink Slip performance. “You can do little Hansel and Gretel trails with things that they like” to create “harmony” between the characters, O’Brien says.
For instance, at the rehearsal, Anna stuns in a white Staud mini dress featuring a beaded dolphin design (reflecting Harper’s love for the ocean) while Harper wears a lavender L’Academie vest set (reminiscent of Anna’s pink The Frankie Shop set). Likewise, Lily wears a pistachio green blazer and matching shorts (nodding to Tess’ professional monochromatic outfits) and Tess wears a youthful custom-made ruched fuchsia dress, which O’Brien says pays homage to Curtis’ look in her 1983 film Trading Places. “We wanted it to feel super out of place like she was doing it just bug people,” explains O’Brien, adding: “I know she didn’t love wearing it but I think it made sense because it was just so elaborate and extreme and punchy, which is her [Lily’s] entire voice at that luncheon.”
Unsurprisingly, the short-but-sweet wedding scene is packed with statement looks. Beyond Anna’s refined Prea James gown, Eric complements her in a classic Tom Ford tuxedo, Tess shows up and out in a blue Halston gown, and the bridesmaids (including Harper, Lily, and Pink Slip members) stun in floral Reformation dresses.
But the cherry on top of this scene is the best Easter egg of them all: Jake (Chad Michael Murray) brings a young Tess lookalike as his wedding date. And she’s wearing Tess’ post-makeover Diane Furstenberg printed dress from Freaky Friday… with some modifications.
“It was not something that we had. And I asked to get in the Disney vault, but it wasn’t something that they could give me,” O’Brien reveals. After thrifting the dress, which was too small, O’Brien says: “We opened it up, we added gussets. I found fabric that looked similar, and we just made it work. I did the silly little star necklace and I put her in similar sunglasses. We all came together and I think it turned out pretty good.”
Additional custom looks like Tess’ pickleball tournament activewear, Harper’s T-shirt for a made-up band “Pantheress,” and Ella’s sparkly final performance dress add even more color and whimsy to the movie. But the high-end finds (from Moschino to Manolo Blahnik) really amp up the style and unexpectedly cements it as a fashion-girl film, leaning into 2003 nostalgia while embracing today’s fashion landscape.
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