Top CrossDressing Movies to Watch in 2023

While the volume of films featuring cross-dressers and general LGBTQ characters is not as huge as it should be in 2023, the progress made over the recent years is worth appreciating.

The more we speak of the films that portray the cross-dresser experience in a good light, the more their numbers will soar.

With lots of emotions and plot twists in the mix, we have curated a list of the best crossdresser movies that thoughtfully capture the feelings that encapsulate the cross-dresser experience.

Worth noting is that while these films may not tell the story of all cross-dressers, they all carry crucial messages.

Transfariana (2023)

This film by French director-come-photographer tells tales of the unorthodox collaboration between FARC–the disbanded Colombian guerrilla group–and the transgender activist movement in Columbia that birthed the new local laws.

The trailer opens with Jaison Murillo introducing himself as a FARC guerrilla member and a political prisoner.

He recounts how he and Laura–a trans woman–met and established a relationship when she was transferred to his prison compound.

While his actions earn him an expulsion, the punishment forces him to fight for change.

Transfariana is an impactful documentary that will get you to immediately fall for the unusual romance between a former trans sex worker and a FARC soldier all through the 90 minutes.

Everybody’s Talking About Jamie (2021)

Everybody’s Talking About Jamie is a familiar coming-of-age story based on real-life events.

A young boy called Jamie yearns for more than his working-class Brirush city.

His mother, Margaret, does her best to be there for him even as he faces hostility for being gay from his classmates, a teacher, and even his father, who disowns him.

But instead of hiding his true self, Jamie decides to pursue his life-long dream–to become a drag queen.

He does this with the help of his best friend Pritti and drag mentor Hugo.

As he faces the realities of his would-be life, Jamie has much growing up to do.

He needs to learn to walk in heels and craft an on-stage persona, among other things.

Director Jonathan Butterell’s dream sequences that tell more of Jamie’s story do not disappoint.

Still, the movie’s highlight has to be when Hugo lets Jamie into his past as Loco Chanel and what his gay community underwent in the wake of the AIDS crisis, which took with it the life of Freddie Mercury and Hugo’s lover, among many others.

Trade (2019)

An adaptation of David Kaye’s book ‘Boulevard Girls’, Trade follows the lives of two men.

One is a straight-laced lawyer, and the other a streetwise hustler whose paths cross, leading to a relationship that opens their eyes to who they really are.

Michael (played by Austin Miler) is a good-looking, thriving lawyer who has been convincing his wife to have a child with no luck for years.

The only problem, however, is that he has this undying need to dress like a woman and sleep with men, and these desires come to life when he meets Shawn (played by Ashanti Mozelle), who encourages him to be his true self.

How will Michael’s wife react when she soon discovers a set of women’s clothes in the boot of their car?

All this is told beautifully in the 113-minute film that perfectly blends authenticity, good visuals, and excellent acting.

The Stroll (2023)

The brainchild of Zackary Ducker and Kristen Lovell, ‘The Stroll’ is an evocative documentary about transgender women of color during the 1990s and early 2000s. These women engage in sex work in The Stroll, an area in the Meatpacking District of Lower Manhattan.

Theirs is a story of despair, triumph, and sisterhood.

From when the film begins, with women not afraid to reclaim their narrative, to the middle, where haunting and harrowing experiences are revealed right to the end, where we smile as we see these women drawing out their confidence in themselves and helping each other, The Stroll sure takes you through a roller coaster of emotions.

The highlight of this documentary is Sylvia Rivera, a trans sex worker, activist, and crucial player in the Stonewall Inn uprising.

Solo (2023)

Directed by Canadian Sophie Dupuis, ‘Solo’ is a queer romance drama revolving around the life of Simon, a fast-rising star in the Montreal drag queen scene.

He has a complicated relationship with his mother, who has been gone for 15 years, and has a passionate but toxic crush on Oliver.

During the 101 minutes through which this film runs, the producer of two critically acclaimed films ‘Family First’ and ‘Underground’ attempts to explore the roots, mechanisms, and consequences of toxic love relationships, attempting to dissect why someone can stay with an abusive person and still be convinced they are in love.

We love that the film brings together queer actors, something that is crucial for contributing to the film’s realism.

Will Simon drown himself trying to seek the validation of the two people he loves most?

Or will he realize he deserves better and choose himself? Buckle up, as this is going to be a wild ride.

Mutt (2023)

‘Mutt’ sees director Vuk Lunglov-Klotz navigating personal transition through a comprehensive lens.

In Klotz’s feature debut, time never seems to slow down for his lead character, Feña, a trans man battling prejudice and everyday issues in New York.

He bumps into an old ex-boyfriend, John, at a club, and they reconnect, but he leaves coldly after a night of pleasure.

What follows is an ever-ending list of problems like his younger sister showing up unannounced, his bank refusing to cash his check, and his friend disappointing him.

The film highlights the trans intensified by the city’s density.

We are shown how Feña is often misgendered, asked insensitive questions by strangers, and ostracized by those he deems family.

However, we also get to see the easy, laid-back moments where the characters just breathe and bond, especially the scenes where Feña spends time with Zoe, his sister.

Overall, it is a film with frenetic energy and lots to deliver and, above all, a character we all root for from beginning to end.

What to Wear on a Movie Date

Have you identified a cross-dressing movie that you’d enjoy watching?

It might be time to go on that movie date and dress the part.

If you want to look more feminine to match the movie vibe, then go for it.

But first, remember always to wear an outfit that makes you comfortable and showcases your style sense.

Another practical tip is avoiding very tight-fitting pants since you will be seated in one place for hours, so comfort is key.

Looking for outfit inspiration?

Here are some suggestions:

Puffer Vest and Leggings

If you’re edging towards a comfortable and flattering style, this is the way to go.

Throw on some vinyl or leather leggings and accompany them with a long-sleeved top before finishing the look with a stylish puffer vest.

As for footwear, bring in your favorite to further anchor your look and accessorize with a crossbody purse and round sunglasses.

Slim-Fitting Jeans and Sweater

Consider tight-fitting jeans and a comfy sweater for a cold winter movie date.

Pair this look with heeled boots and throw on a winter hat.

If you are feeling particularly sexy, a bright lipstick shade will help unleash the diva in you.

Ripped Jeans and a Tank Top for a Casual, Flirty Look

Whether you just want to feel beautiful or plan to take your date home with you tonight, you can never go wrong with a casual, flirty look.

Try pairing your favorite ripped jeans with a corset or sleeveless tank top to give your outfit an element of swag.

For this look, flats or sneakers would be a great addition.

Also, remember to throw on that wig that flows to your shoulders.

Jeans and Blazer for a Feminine Casual Look

Another movie date outfit inspiration idea is feminine casual.

You will need a pair of jeans, a blazer, and a colorful scarf with boot heels to enhance the look.

Be bold and throw in a pair of cute earrings and a wristwatch.

Alternatively, you could opt for a lace dress that goes well with your favorite pumps or heels.

Pair this up with a purse-style back and some makeup.

Mesh Tank Top

If you are feeling yourself and want to show some skin (actually, lots of it), you could go for a mesh tank top and shorts or a pair of jeans.

You can complete this look with sneakers or mules, although heels will also do the magic.

Bodysuits

Who said you can’t wear costumes to a movie date? If this is the path you want to take, then bodysuits are the answer.

They accentuate your favorite features, creating bulges in the right places.

The bodysuit can cover your waist up, but you could wear shorts or fitting jeans from the waist down.

Bring in a neck chain to complete your look.

Conclusion

Nothing beats sitting back and enjoying a good movie, especially when it tells your story in a way no one else does.

Fortunately for millions of cross-dressers worldwide, there is a huge array of movies they can relate to.

This guide sheds some light on a few of them and gives you some helpful tips on how to dress up and show up for cross-dressing movie dates.