7 Freakier Friday costume easter eggs that make the sequel even more iconic than the original film

Cosmopolitan

2 days ago

22 years after Freaky Friday made its way onto our screens, Disney has released a sequel, Freakier Friday, in cinemas Friday, 8 August. All the original cast are back – yes, even Chad Michael Murray – alongside a few new faces, too, for one of the most anticipated films of 2025.
Lindsay Lohan's Anna is juggling parenting her teen daughter, Harper, with her job as a music exec. She's also attempting to seamlessly blend her family ahead of her imminent wedding to Eric, whose daughter Lily is Harper's classmate. Unfortunately, despite help from Jamie Lee Curtis' Tess, she's struggling and, er, largely failing. Cue psychic, Madame Jen, getting involved, resulting in a four-way body swap between Anna and Harper, and Tess and Lily. (Don't worry, Pei-Pei and her mum do still make a cameo, just sans fortune cookies!)
Alongside more of the same chaotic antics, fashion is a central theme throughout the sequel, not least because of Lily's desire to be a fashion designer. Plus, per any good rom-com, there's an outfit montage featuring Anna, Tess and budding pop star, Ella, portrayed by Maitreyi Ramakrishnan.
We sat down with dcostume designer, Natalie O'Brien, to chat about working with the all-star cast, honouring the original film, and staying true to the characters' identities while navigating how much fashion and culture have changed in the past two decades.
Kind of scary, honestly. I grew up with Freaky Friday. I wanted to do it right, and wanted to honour [the original] correctly and pave the rest of this legacy.
For Anna [Lindsey Lohan], I was looking up rocker moms. For Tess [Jamie Lee Curtis], different therapists that were kind of chic. I went to the Brentwood Country Mart, and I was watching all these women with their scarves and their Jenni Kayne button-up cardigans and their big boho bags – I was getting really inspired by them.
I grew up in San Diego, by the beach, so I would go and watch all the surfers and try to understand what Harper would wear and tie in any California vibes. For Lily, I was looking on Instagram a lot, and seeing what young, 15-year-old girls are wearing. [I was] playing with old posh punk because she's English, seeing designers like Vivienne Westwood and drawing different characteristics from them.
I was also inspired by our actors themselves. They really brought in this beautiful part of the puzzle.
I'd say a lot. We definitely had some nice, long, healthy fittings for each one. Weirdly, actually, I think we only had three fittings for Jamie. She doesn't love a fitting, she's like, 'I want to just put it on!' She's a legend. Her and I, we collaborated a lot.
We started doing some of the fittings before the character read, and as we started chiselling in different things, some of the writing would change. For instance, the blue Reiss two-piece suit Jamie Lee wears [after the body swap]. In the original script, she had scissors and she was going to cut her hair. I was like, 'Let's cut the blazer' because Lily would wear raw edges.
I remember Lohan wanted to wear her sneakers in one [scene] too, to feel more in character.
That was super big for me. They have their own particular style, so that when they do the switch, it's not not obvious. But I didn't want it to be an over exaggeration, whatever is in these closets has to make sense for the characters. I was trying to think through their brains – they're trying to be this [other] character. It turned into this really fascinating way of thinking.
I remember the orange Balenciaga rash guard moment, with the blazer and Re/Done shorts and her Adidas that Anna [as Harper] ended up in. Like, [Harper] would wear a rash guard to work! She's this surfer girl stuck in her [mum's] body.
It's tricky to have a 66-year-old therapist and a 15-year-old fashionista and somehow turn them into something that is cohesive in themselves, but not inappropriate. It was definitely out of Jamie's wheelhouse to be in these outfits. She told me over and over again, 'Hmm, I don't know [about this outfit].' I'm like, 'Let's just do it,' and [the clothes] really got her into character.
Jamie Lee's teddy bear overalls. We made this little headband with the teddy bear falling off of it. The legend that Jamie Lee Curtis is, she went out there and she did the freaking splits. I don't remember if you see that in the film, but I definitely have photos of her doing the splits in these overalls.
Jamie and Lindsay's outfits that they wear from the photoshoot was a tricky one. I was told this needs to be the most heightened outfits of the film, [which was] a lot of pressure. It had to be something that was runway and extravagant and wild, something that's gonna blow Chad Michael Murray's socks off. We also needed multiples because we had stunt doubles for the car.
I was baffled for a while. But it was kind of serendipitous, in a way, that we found two of the Christopher John Rogers dress and Jamie Lee's Cinq à Sept outfit. It also heightened their acting. Like, Anna on the table, flipping her hair around in this dress and struggling with it, the gloves are falling down. It's not as crazy and fun and funny if she's in jeans. Then you see Tess crawling on the floor with all of these punk-ish pins and her giant cinched-in waist belt, and you can tell she is uncomfortable because Lily dressed everybody.
When the costumes can make your actor have a more exciting time and be able to play with their characters, that's really what I'm looking for.
Yeah, it was a lot of prep. Once we figured out [Ella's album] was 'Hungry,' we made it food-oriented. I found everything at the costume shop – we had strawberries, grapes, the big cake, a hot dog.
Then there was this silly balloon dress. I blew up all those balloons myself! We didn't know that Maitreyi was deathly afraid of balloons popping. It wasn't written in the script that she was going to pop them, but once we put the balloon dress on her, I remember her asking me for a safety pin. I was like, 'What are you gonna do with the safety pin? I don't have a reset, so you get a one-and-done.' When she started popping [the balloons], her scream is a real scream of fear.
There's a lot of stuff cut out – there were about 15 changes total. I had different setups with different outfits under to do fast changes. It kind of felt like theatre that day. It was really cool, really fun.
I'd say at least 70% was purchased and rented. Some of the stuff was custom, like the band shirt we made. I felt like it would be something that was in Anna's closet. It was a fake band, which I liked, because otherwise it might be distracting. We ended up making the Converse that Harper wears. They have this little surfer girl on, and it says Harper down the back. They're very cute, but you don't really catch it.
The hat that Harper wears [in the detention scene] is Farm Rio. I had totally worn it to Greece before. I had those hats in my own closet, they were mine! The script said giant hats and I was like, 'I have the perfect hat, Anna would totally wear this hat on a vacation.'
It was all kind of custom stuff for Maitreyi. We designed and made her performance outfit. I thought it was a nod to the Katy Perry, Olivia Rodrigo and Sabrina Carpenter world that is current right now. Olivia was a big [inspiration for Ella], and I was very excited to touch on that. We did the floating tie, which would be kind of weird normally, but it's so something Lily would do to feel cool and kind of punk. We worked with props to make all of Ella's tour merch, too. There was so much, I kept a lot of it.
It was not the actual Diane Von Furstenberg dress. We couldn't get it from the Disney vaults. It was written in the script, so I knew I had to get it, but it was a very difficult hunt.
I ended up finding it on eBay. It was not cheap, and it was not the right size. We had to make gussets and placards and open it up completely for it to fit our Tess look-alike. It makes me so happy to be able to honour the costumes [from the original film]. It's a designer's dream.
There's a moment when they're all in the bedroom and they're trying different stuff on, and Lohan ends up wearing this black, asymmetrical dress. It's actually Isabel Marant. I was trying to nod to what she wears when she's on stage with Pink Slip [in the original].
The colour story for the Christopher John Rogers dress matches the red and black [from the original film poster]. That's why we did the gloves. Even just the flower choker keeps the same uniformness as the guitar pick choker.
I wanted to put in some tartan and some plaids, because that's on the original poster. [For the pickleball tournament] Jamie wanted to wear black and I was like, 'No, Lily would not wear black and you're Lily [in this scene].' She was like, 'I look good in black, but okay, I trust you, do what you want to do,' really respectful and beautiful. She's in pink plaid, I made this little skirt and tie, got her little pink glasses and a pink visor. It kind of felt like a Clueless moment, a nod to that. This film is nostalgia, it was a huge part of my childhood.
The dress Jamie Lee wears as Lily for the brunch is a nod to her Trading Places dress, a ruched pink dress. I was like, 'Why don't we design something? We can cover the arms and build this Gaultier-style bra underneath,' which we did through Trashy Lingerie in LA. So we did, we made that dress for her.
There's a scene – it was cut out – but Chad Michael Murray's in head-to-toe denim, and I wanted that to be an homage to the Backstreet Boys or NSYNC. He loved this outfit so much!
I kept the OG leather jacket for Chad Michael [like he wore in the first film]. He needed to have it. I think that's important – to make the audience feel like they're a part of the original, but 20 years later.
Also, so much fun that man! He's so wonderful and so incredible. I remember showing him a rack of leather jackets in the fitting, and he tried them all on. He ended up with a good old AllSaints jacket, that's what he gravitated towards.
The star boots Harper wears are from this brand called Modern Vice. I wear them every single day – they're my own, I've bought these boots. Jamie Lee was obsessed with her boots, so I reached out to Modern Vice and I got a pair made for her and I gave them to her. I don't think she wanted to have any of the crazy, wild things. Jamie Lee was like, 'I never want to put this on again!'
I gave Harper her bracelet that had little woven waves on it as a gift, too.
I would be so lucky to be able to do an even freakier, freakiest Friday. If they would have me, I would be honoured!
Alexandria Dale is the Digital Fashion Writer at Cosmopolitan UK. Covering everything from the celebrity style moments worth knowing about to the latest fashion news, there's nothing she loves more than finding a high street dupe of a must-have designer item. As well as discovering new brands, she's passionate about sustainable fashion and establishing the trends that are actually worth investing in. Having worked in fashion journalism for six years, she has experience at both digital and print publications including Glamour and Ok!