Movies like Dressing Up
The best movies like Dressing Up are Can't Buy Me Love (1987), Ladies First (2026) and Don't Hug Me I'm Scared 5 (2015). If Dressing Up hooked you, these 20 similar films are what to watch next, and every pick says why it matches.
Dressing Up
Quick picks
- Highest ratedThe Elephant Man (1980)8.1/10 from 4,129 votes
- NewestLadies First (2026)Released 2026
Can't Buy Me Love (1987)
Nerdy high schooler Ronald Miller rescues cheerleader Cindy Mancini from parental punishment after she accidentally destroys her mother's designer clothes. Ronald agrees to pay for the $1,000 outfit on one condition: that she will act as though they're a couple for an entire month. As the days pass, however, Cindy grows fond of Ronald, making him popular. But when Ronald's former best friend gets left behind, he realizes that social success isn't everything.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisLadies First (2026)
An arrogant but charismatic ladies' man finds his life of money, power and casual flings upended when he wakes up in a parallel world dominated by women.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisDon't Hug Me I'm Scared 5 (2015)
The two remaining puppets learn about eating healthy, but things go awry when they receive a mysterious phone call.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisWatching the Detectives (2007)
Neil, a self-proclaimed film geek and owner of Gumshoe video, has always been content to live vicariously through his favorite films noir. But when he meets Violet, a real-life femme fatale, his mundane world gets turned upside down and the line between reality and the movies quickly begins to blur.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisJust One of the Guys (1985)
When Terry Griffith loses her high school's writing competition, she's convinced that it's because she's a girl. So Terry decides to change high schools and pose as a boy to prove her point. Her brother, Buddy, helps her pass as a guy so well that she is soon making friends with the boys at school, including the attractive Rick, who becomes her new best friend. But her gender-swapping makes things difficult when she falls in love with him.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Hot Chick (2002)
Not only is Jessica Spencer the most popular girl in school -- she is also the meanest. But things change for the attractive teen when a freak accident involving a cursed pair of earrings and a chance encounter at a gas station causes her to switch bodies with Clive, a sleazy crook. Jessica, in the form of the repulsive Clive, struggles to adjust to this radical alteration and sets out to get her own body back before the upcoming prom.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Shape of Things (2003)
Quiet, unassuming Adam is changing in a major way, thanks to his new girlfriend, art student Evelyn. Adam's friends are a little freaked by the transformation.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Boy in the Dress (2014)
Dennis feels different - an ordinary boy in an ordinary house in an ordinary street, playing football with his mates and living with his dad and brother, but frustrated by the boring grey world he inhabits. Life has never really been the same since his mum left. However, transformation can happen in the most unexpected places. Aided by Lisa, the coolest girl in school, Dennis creates a whole new persona and puts it to the ultimate test - but can a boy wear a dress, and what will the headmaster, his dad and his friends on the football team think if they find out?
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Night Before (1988)
A popular beauty surprisingly asks a nerd to take her to the prom. He wakes up hours later in a sleazy alley. She's missing but he remembers nothing about it.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisGypsy (1962)
Gypsy's mother Rose dreams of a life in show business for her daughters, but Louise becomes a huge burlesque star. Stage musical loosely based on the memoirs of Gypsy Rose Lee.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisDumplin' (2018)
To prove a point about measuring up and fitting in, Texas teen Willowdean “Dumplin’” Dickson enters a local pageant run by her ex-beauty queen mom.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisUglyDolls (2019)
In the adorably different town of Uglyville, weirdness is celebrated, strangeness is special and beauty is embraced as more than meets the eye. After traveling to the other side of a mountain, Moxy and her UglyDoll friends discover Perfection -- a town where more conventional dolls receive training before entering the real world to find the love of a child.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisWhat's New Pussycat? (1965)
A playboy who refuses to give up his hedonistic lifestyle to settle down and marry his true love seeks help from a demented psychoanalyst who is having romantic problems of his own.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisI Feel Pretty (2018)
A head injury causes a woman to develop an extraordinary amount of confidence and believe she's drop dead gorgeous.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Count (1916)
A tailor's apprentice burns Count Broko's clothes while ironing them and the tailor fires him. Later, the tailor discovers a note explaining that the count cannot attend a dance party, so he dresses as such to take his place; but the apprentice has also gone to the mansion where the party is celebrated and bumps into the tailor in disguise…
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisMask (1985)
A significantly deformed but highly intelligent teenage boy and his biker gang mother attempt to live as normal a life as possible under the circumstances.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisMoxie (2021)
Inspired by her mom's rebellious past and a confident new friend, a shy 16-year-old publishes an anonymous zine calling out sexism at her school.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisThe Elephant Man (1980)
A Victorian surgeon rescues a heavily disfigured man being mistreated by his "owner" as a side-show freak. Behind his monstrous façade, there is revealed a person of great intelligence and sensitivity.
Why it matches: Recommended by TMDB viewers
Absolute CinemaMovies like thisEmpire Waist (2024)
Lenore Miller’s size has always earned her teases and jeers in her school’s hallways, but this clothes-loving teenager is about to set the world on fire with her own line of inclusive fashion designs.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisA Boy Named Charlie Brown (1969)
Poor Charlie Brown. He can't fly a kite, and he always loses in baseball. Having his faults projected onto a screen by Lucy doesn't help him much either. Against the sage advice and taunting of the girls in his class, he volunteers for the class spelling bee.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like this
Like Dressing Up and something else?
Blend two favourites and we’ll find the films in between.
Frequently asked questions
What are the best movies like Dressing Up?
The closest matches to Dressing Up are Can't Buy Me Love (1987), Ladies First (2026) and Don't Hug Me I'm Scared 5 (2015). Below are 17 more, each with the reason it matches.
What should I watch after Dressing Up?
Start with Can't Buy Me Love (1987), the closest match to Dressing Up.
What is the highest-rated movie like Dressing Up?
The Elephant Man (1980), rated 8.1/10 by 4,129 TMDB users.
What is the newest movie like Dressing Up?
Ladies First (2026) is the most recent release on this list.
Are there English movies like Dressing Up?
Yes: Can't Buy Me Love (1987), Ladies First (2026) and Don't Hug Me I'm Scared 5 (2015).
How are movies similar to Dressing Up chosen?
First come films that Trakt’s viewers watch alongside Dressing Up, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.