Back in 2003, before Mean Girls had us chanting “On Wednesdays we wear pink,” Lindsay Lohan was introducing an entirely different style philosophy. Her role as Anna Coleman in Freaky Friday brought the early 2000s “mall punk” aesthetic to mainstream Hollywood: band tees, studded belts, arm warmers, and those iconic low-rise pants. It was grunge-lite, rebellious yet relatable, and it defined a generation of teens eager to express their edge.
Now, two decades later, Lohan is back — this time in Freakier Friday, the highly anticipated sequel that reunites her with Jamie Lee Curtis and expands the body-swapping chaos to a whole new cast. But make no mistake: just like the original, this sequel doesn’t just promise laughs and heartfelt family lessons. It also delivers a feast of fashion moments that blend nostalgia with modern flair.
Revisiting an Iconic Wardrobe
The original Freaky Friday costume design, dreamed up by Genevieve Tyrrell, struck gold by capturing two sides of early 2000s life: the rebellious teen who raided Hot Topic and the polished, suburban mom whose Banana Republic wardrobe carried unexpected chicness. Together, those styles became cultural shorthand for youth angst and adult responsibility.
For the sequel, Lindsay Lohan herself has leaned into that fashion legacy. During the press tour, she’s been spotted wearing looks that nod directly to her character Anna’s Y2K outfits — a clever wink at fans who grew up idolizing her as the ultimate cool-girl teen. Her stylist Andrew Mukamal, best known for orchestrating Margot Robbie’s Barbie press tour wardrobe, has made sure that nostalgia is baked into every red-carpet appearance.
A Fresh Vision by Natalie O’Brien
Stepping into the shoes of the original’s costume designer, Natalie O’Brien (Hustlers, Zola) took on the daunting challenge of reimagining Freaky Friday’s fashion for today’s audience. And according to her, it was a monumental task.
“It was a big fashion film, one of the bigger things I’ve worked on,” O’Brien explained in an interview. “You’re dressing Lindsay Lohan, and she’s an icon. Her style, the way she wears clothing, the elegance she brings — you need endless options to make it work while also keeping it timeless.”
How endless? By O’Brien’s estimate, Lohan alone cycles through at least 45 different outfits across the film. That sheer volume means audiences won’t just get Easter eggs from the original but also a full runway of looks to obsess over.
Anna 2.0: The Rocker Mom
In Freakier Friday, Anna Coleman has traded her teen angst and garage band guitar for a career in the music industry — now as the manager of Ella (played by Never Have I Ever breakout Maitreyi Ramakrishnan). But O’Brien knew Anna couldn’t lose her signature edge.
“She wears blazers now, but she still has that rocker core,” O’Brien explained. “I wanted her to feel like a cool mom, because that’s so honest to the storytelling.”
That translated into bold details and statement pieces: panther-print silk pajamas, vintage blouses paired with studded boots, and glittering mesh dresses. Each look bridges her past with her present, signaling a woman who’s grown up but hasn’t lost her spark.
Tess 2.0: The Chic Therapist
Jamie Lee Curtis’s Tess Coleman is still a therapist, but this time she’s expanded her career into the media world, hosting a podcast and publishing a book. For O’Brien, that meant evolving Tess’s wardrobe while staying true to her character’s calm, grounded energy.
“She’s a California therapist now,” O’Brien said. “I wanted her to feel beachy, monochromatic, and effortlessly cool — like one of those chic Brentwood grandmothers who still look like they just stepped out of Erewhon.”
The result? Sleek neutrals, linen sets, soft knits, and minimalist jewelry that convey wisdom and modern sophistication without losing approachability.
New Characters, New Fashion
This time around, the body-swap plotline includes two new characters: Anna’s daughter Harper (Julia Butters) and her soon-to-be stepdaughter Lily (Sophia Hammons). With four characters swapping identities — and wardrobes — the fashion game naturally got trickier.
Each look needed to reflect the original personality of the character while also being believable when worn by someone else. That meant O’Brien and her team had to design clothes that could do double duty: making sense in context, but also visually hilarious (or surprisingly fitting) when swapped.
Fashion as Storytelling
What makes Freakier Friday stand out isn’t just its comedic premise but the way fashion continues to act as a storytelling device. Clothes don’t just make the characters look good; they highlight identity, evolution, and the way relationships shift across generations.
Anna’s wardrobe shows us a woman who’s matured but still embraces her creative edge. Tess’s style mirrors her personal growth into a confident, modern professional. And the new characters bring youthful energy and fresh dynamics that expand the fashion palette.
In other words: the sequel is proof that fashion isn’t just window dressing. It’s part of the plot.
A Legacy Worth Revisiting
Twenty years ago, Lindsay Lohan’s Anna made teenage rebellion look stylish and aspirational. Today, with Freakier Friday, the costumes remind us that identity is ever-evolving, and our wardrobes evolve with us. It’s nostalgia mixed with reinvention — the perfect formula for a sequel that honors the past while carving out its own space.
And if the first film left you wanting to raid your local mall for studded belts, don’t be surprised if this one sends you hunting for panther-print pajamas or breezy California neutrals. After all, as Freakier Friday proves, fashion might just be the most magical switch of all.
