Drew Barrymore on '50 First Dates' outfit: 'I never knew I'd get so sick of it'
Synopsis
Drew Barrymore has confessed she grew deeply tired of the pink T-shirt and white pants she wore every day for four months on the set of '50 First Dates' — the outfit that became one of the most recognisable looks in early-2000s romantic comedy. The admission, made on her own talk show amid a Halloween chat, is a rare glimpse at the quiet monotony behind an iconic on-screen image.
Key Takeaways
Drew Barrymore revealed on The Drew Barrymore Show that she wore the same pink T-shirt and white pants every day for four months while filming 50 First Dates .
She said she 'never knew' she would grow so tired of the outfit, which has since become iconic from the 2004 romantic comedy.
50 First Dates was directed by Peter Segal and co-starred Adam Sandler .
Barrymore also admitted she has not dressed up for Halloween in a long time, despite it being her favourite holiday.
She described a preference for masks, citing anonymity, and naming Darth Vader as her 'first crush.'
Drew Barrymore has opened up about the unexpected fatigue of wearing the same outfit every single day for four months while filming the 2004 romantic comedy 50 First Dates, telling her audience she never anticipated how quickly an iconic look could lose its charm.
The Pink T-Shirt That Wore Out Its Welcome
Speaking on The Drew Barrymore Show, the Hollywood actress reflected on the now-recognisable costume from the film — a simple pink T-shirt paired with white pants — that became inseparable from her character. 'Oh, the pink T-shirt, white pants. Boy, I never knew I'd get so sick of that outfit. We had so many of those pink T-shirts and white pants. And every day for four months, I wore those pink T-shirts and white pants. Boy, I never knew I'd get so sick of that outfit,' Barrymore said.
The remarks came during a conversation about Halloween and her longstanding love of costumes — a topic that prompted her to revisit the wardrobe memories from the film set.
About the Film
50 First Dates, directed by Peter Segal, stars Barrymore opposite Adam Sandler. The film centres on Henry Roth, a marine veterinarian who falls for art teacher Lucy Whitmore, only to discover she suffers from a memory condition that causes her to forget him each time she falls asleep. Undeterred, he resolves to win her over anew every single day. The film was a commercial success on its release and has remained a nostalgic favourite among romantic comedy fans.
Barrymore on Halloween: Masks, Anonymity, and Darth Vader
When an audience member asked about her plans for Halloween 2026, Barrymore admitted she had not dressed up in a long time — something she herself called 'so stupid' given that it is her favourite holiday. 'Halloween is like, oh no, you can come from whatever background and just be the freak you are. And you don't have to get someone something,' she said.
She also revealed a preference for masks, citing anonymity as part of their appeal. 'Darth Vader was my first crush and anybody can be anonymous in a mask. And so that's kind of pleasant,' she added, describing her low-key approach of picking up a mask from a local pharmacy and building an outfit around it.
The Enduring Pull of Costume and Character
Barrymore's candid recollection highlights a rarely discussed side of filmmaking: the physical and psychological monotony that can come with continuity-driven costuming. Actors shooting over extended periods in fixed costumes often cite wardrobe repetition as one of the more underappreciated challenges on set. For Barrymore, the pink T-shirt and white pants have since taken on a life of their own as a pop culture touchstone — worn by fans at themed events and Halloween parties for two decades.
Whether Barrymore ultimately suits up for Halloween this year remains to be seen, but her mask philosophy suggests any costume she does choose will keep her identity pleasantly hidden.
Point of View
Yet the actress who made it iconic spent four months longing to be rid of it. There is a broader truth here about how continuity costuming — a largely invisible craft decision — shapes audience memory in ways that outlast the production itself. For a talk show segment, it lands with more cultural weight than it might appear.
NationPress
27 Oct 2026
Frequently Asked Questions
What did Drew Barrymore say about her '50 First Dates' outfit?
Drew Barrymore said she wore the same pink T-shirt and white pants every day for four months during filming, and grew far more tired of the look than she ever expected. She made the remarks on The Drew Barrymore Show during a Halloween-themed conversation.
What is '50 First Dates' about?
'50 First Dates' is a 2004 romantic comedy directed by Peter Segal, starring Drew Barrymore and Adam Sandler. It tells the story of a marine veterinarian who falls for an art teacher with a memory condition that causes her to forget him each day, prompting him to win her over repeatedly.
Is Drew Barrymore dressing up for Halloween this year?
Barrymore admitted on her show that she has not dressed up for Halloween in a long time, calling it 'so stupid' since it is her favourite holiday. She said she typically picks up a mask from a local pharmacy and builds a simple costume around it.
Why does Drew Barrymore like wearing masks for Halloween?
Barrymore said she values the anonymity that a mask provides, adding that 'anybody can be anonymous in a mask.' She also mentioned that Darth Vader was her 'first crush,' suggesting a lifelong affection for masked characters.
Who directed '50 First Dates' and when was it released?
'50 First Dates' was directed by Peter Segal and released in 2004. The film starred Drew Barrymore opposite Adam Sandler and has remained a popular romantic comedy two decades after its release.
