How ‘Freakier Friday’ Continued The Fashion Legacy Of The Original Film

In 2003, a year before Lindsay Lohan had us wearing pink on Wednesdays, she inspired us to channel our inner mall punk with band tees, low-rise work pants, and studded belts. Yes, this is in reference to Freaky Friday, the beloved Disney film in which Lohan starred opposite Jamie Lee Curtis as Anna and Tess Coleman, a mother and daughter who are at odds — and who, through a magical twist, switch bodies. The film’s wardrobe, created by costume designer Genevieve Tyrrell, helped crystallize early 2000s teen punk aesthetic, but also gave us some surprisingly chic mom style to aspire to.

The original film’s influence is so enduring that during the press tour for the much-anticipated sequel Freakier Friday, Lohan has been spotted in red carpet looks that nod directly to her character Anna’s original outfits. (Her stylist is Andrew Mukamal, who famously dressed Margot Robbie for the Barbie press tour.) The sequel reunites Lohan and Curtis while expanding the body-swap chaos to include two new characters: Anna’s daughter Harper (Julia Butters) and her soon-to-be stepdaughter Lily (Sophia Hammons).

With four characters swapping lives — and wardrobes — there are plenty of new outfits for us to obsess over and maybe even re-create. This time around, costume designer Natalie O’Brien is at the helm, bringing a fresh, modern edge to the film’s sartorial legacy. “It was a big fashion film, one of the bigger things that I’ve worked on, with so many different changes,” O’Brien tells TZR. “You're dressing Lohan, and she's an icon with her style and the things that she wears, and the way that she’s so elegant with her clothing,” she says. “You have to have so many different options to be able to make it work, but also make it transcend and be timeless.” She estimates Lohan alone had at least 45 wardrobe changes.

O’Brien began her process by putting together what she thought would make sense for each character’s identity, especially given the film’s core conceit of identity swapping. Former Pink Slip guitar goddess Anna is still in the music industry, but now as the manager for Maitreyi Ramakrishnan’s pop star Ella, so, even though she wears business blazers, O’Brien made sure she didn’t “totally lose her rocker edge.” That meant bold, unexpected details from Anna’s looks, from panther-patterned silk pajamas, vintage blouses with studded boots, and sparkly mesh dresses. “She's like a cool mom,” says O’Brien. “I didn't want to take that away from her because that’s so honest to the storytelling.”

A similar approach was taken with Tess, who’s still a therapist, but now also hosts a podcast and has a new book coming out. “She’s a California therapist, so I wanted to keep her beachy and monochromatic and kind of cool, like one of those chic Brentwood country moms or grandmas,” says O’Brien. “You have the characters already, so you're just figuring out the next natural place in their lives and where they’re going to go.”

The newbies, Harper and Tess, are soon-to-be stepsisters who can’t stand each other and couldn’t be more different. Harper is a California surfer girl with a more laid-back style, while London-born Lily is an aspiring fashion designer. “We did a lot of vintage for Harper, because I wanted to use old-school surf brands like old OP [Ocean Pacific Apparel],” says O’Brien. For Lily, whom O’Brien says was her favorite character to dress, she sourced pieces from Vivienne Westwood, aiming to give the teen an “old posh punk” vibe. “It’s hard to dress a relevant 15-year-old girl in this day and age, where fashion is so fast, fleeting, and changing,” she says. “And to do something playful and still designer-y, it’s like, what is that?” One standout piece for Lily: a pair of custom boots printed with a Union Jack on the back. “That look really served for me,” says O’Brien. “It put a place marker — like, she’s not kidding around. She’s dressed up, she’s going for it. And I think Sophia really rocked it.”

Then, of course, there’s the body-swap element, which presents its own unique challenge, but O’Brien says Lohan was incredibly collaborative, making the big switcheroo much easier to pull off. “We would send each other images, and trying to find that first switchover look was really something that we wanted to pin down correctly, because we have to sell to the audience that she is Harper stuck in Anna’s body.” The look came together with a Balenciaga rash guard, Re/Done Bermuda denim shorts, Adidas sneakers, and a Djerf Avenue blazer, giving serious Blue Crush–meets–Working Girl energy.

While Tess in Lily’s body meant scarves and eyeglass chains, the reverse was decidedly edgier. “I’m shocked they let me do some of the things we did, quite honestly,” admits O’Brien. “I told everyone [at the premiere], ‘Wow, I can't believe you allowed me to put you in this tiny little dress with a bustier underneath, and do cutout finger holes and giant, high denim boots for Jamie to look like a 15-year-old.” O’Brien says Curtis was definitely out of her comfort zone, and she wasn’t afraid to let O’Brien know that when they ran into each other, post-filming. “She was like, ‘I hated it all, but it all made sense.’ I said, I know, but you're a 70-year-old woman looking like a 15-year-old. How else are we supposed to do this?” she laughs.

O’Brien turned to brands like DÔEN, Ganni, Chopova Lowena, Coach, and Mother, as well as LA designers like Aquarius Cocktail and Stickybaby, to dress the cast, but she also built and customized certain looks. One was a sparkly silver star dress worn by Ella during a major performance, meant to reflect one of Lily’s original designs and serve as a tribute to her late mother. Another fun scene includes an over-the-top fashion photo shoot (one that could easily rival the iconic montage from The Lizzie McGuire Movie). “It was an insane day… we had about 19 or 20 outfit changes,” she says. “I made overalls covered in teddy bears, with a matching teddy bear headband, and a balloon dress for Maitreyi. I blew the balloons myself and tacked them onto the dress, then someone started popping them, and we found out that Maitreyi is deathly afraid of popping balloons.” As for Curtis? “Jamie Lee was over there doing the splits, because she is just a magical, wonderful woman who does absolutely everything and can do everything,” says O’Brien. “She was loving it. She was prancing around in these [outfits].”

Of course, there are plenty of Easter eggs scattered throughout the film, both non-costume- (watch for Parent Trap-related cameos and a Mean Girls reference) and costume-related. One was the color palette — O’Brien put Lohan in a red and gray Christopher John Rogers outfit that nods to her original red and black pop-punk look. There’s a Pink Slip band tee, and a custom fuchsia-pink dress that was an homage to Curtis’ look in the 1983 film Trading Places (a favorite of O’Brien’s).

But the biggest costume Easter egg is a look every Freaky Friday fan will instantly recognize: the iconic multicolored silk Diane von Furstenberg dress Curtis wore in the original film. “There’s this funny moment at the end where Chad Michael [Murray] has a date who looks just like Jamie Lee, her name is Bess — like Tess — and she’s wearing the dress,” laughs O’Brien. Finding that dress, however, took some serious sleuthing. “I was heavily stalking Etsy, eBay, and every possible site,” she says. When she finally tracked it down, the look came together with a wig and glasses for what O’Brien calls a “funny, cheeky moment” that only the most loyal fans will catch: “I remember hearing the audience giggling, and I was like, yay, that makes me so happy.”