Movies Like Dressing Up

If you liked Dressing Up, a movie directed by Susan Mogul, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Can't Buy Me Love (1987)
★ 6.9/10
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…
2
Ladies First (2026)
★ 6/10
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.
3
The Hot Chick (2002)
★ 6.4/10
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…
4
Watching the Detectives (2007)
★ 6.3/10
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…
5
Just One of the Guys (1985)
★ 6.4/10
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…
6
Baby Puss (1943)
★ 6.8/10
Tom is dressed up and treated like a baby by the little girl of the house.
7
UglyDolls (2019)
★ 6.6/10
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…
8
I Feel Pretty (2018)
★ 6.4/10
A head injury causes a woman to develop an extraordinary amount of confidence and believe she's drop dead gorgeous.
9
Empire Waist (2024)
★ 7.8/10
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.
10
Dumplin' (2018)
★ 6.8/10
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.
11
The Elephant Man (1980)
★ 8/10
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.
12
Mask (1985)
★ 7.2/10
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.
13
One Chance (2013)
★ 6.7/10
This film follows the remarkable and inspirational true story of Paul Potts, a shy, bullied shop assistant by day and an amateur opera singer by night.
14
The Tramp (1915)
★ 6.5/10
The Little Fellow finds the girl of his dreams and work on a family farm. He helps defend the farm against criminals, and all seems well, until he discovers the girl of his dreams already has someone in her life…
15
Dennis the Menace (1993)
★ 5.9/10
Mr. Wilson's ever-present annoyance comes in the form of one mischievous kid named Dennis. But he'll need Dennis's tricks to uncover a collection of gold coins that go missing when a shady drifter named Switchblade Sam…
16
The Shape of Things (2003)
★ 6.2/10
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.
17
Skater Girl (2021)
★ 7.2/10
Prerna, a teenager growing up in rural India, comes of age when she’s introduced to the sport of skateboarding. As a result, she has to fight the odds to follow her dreams and compete in the national championship.
18
The Dink (2026)
★ 6.4/10
Desperate to save a struggling country club and earn his father's respect, a washed-up tennis pro is compelled to break a sacred vow and do the unthinkable: play pickleball.
19
Cruella (2021)
★ 8/10
In 1970s London amidst the punk rock revolution, a young grifter named Estella is determined to make a name for herself with her designs. She befriends a pair of young thieves who appreciate her appetite for mischief…
20
Gypsy (1962)
★ 6.4/10
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.