10 times male celebrities have worn skirts or dresses – and absolutely nailed it

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By VT

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We all know that Madonna isn't afraid to break boundaries when it comes to fashion, and neither is her 15-year-old son, David Banda.

The teenager proved that gender norms are a thing of the past as he donned a long cream dress in an Instagram video his mother shared online on Sunday. "Confidence is Everything," she captioned the clip.

But David isn't the only one — in fact, there's a slew of male celebrities who are super confident when it comes to rocking dresses and skirts.. Here's just 10 of them...

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(Credit: Instagram / Madonna)

1. Harry Styles

Harry Styles broke the internet earlier in November of 2020 after appearing on the cover of Vogue. The former One Direction star is not only the first solo male to appear on the prestigious magazine's cover, but he did so while donning a dress.

Speaking about his decision to depart from conventional gender norms, he told the publication: "Clothes are there to have fun with and experiment with and play with."

"What’s really exciting is that all of these lines are just kind of crumbling away," he added. "There’s so much joy to be had in playing with clothes. I’ve never really thought too much about what it means — it just becomes this extended part of creating something."

2. David Beckham

David Beckham once wore a sarong with fashionista wife, Victoria Beckham, while the pair was vacationing back in 1998.

While the Daily Mail reports that the former professional football player attracted criticism at the time, Beckham later told ITV's Lorraine that he doesn't regret his sartorial choice.

"Sarongs are great. That's one thing I never regret because I thought it looked great and I would still wear it now," he said. "Over the years it's not just myself, everybody looks back at old pictures of themselves and thinks, 'I can't believe I wore that, or I wish I hadn't worn that, or what was I thinking?'"

3. Kanye West

Back in 2011, Kanye wore a Givenchy leather kilt on his Watch the Throne tour. Writing about the divisive item of clothing four years later, in PAPER, he said that the stye move actually solidified his reputation as a trendsetter.

"I paid my dues when I had to wear a kilt in Chicago, and friends would say, 'What's your boy got on?'," he explained. "There are warriors that have killed people in kilts in the past. Who gets to decide what's hard and what's not hard?"

Well said, Kanye.

4. Kid Cudi

Kid Cudi was praised online after performing on Saturday Night Live while wearing a floral dress on Saturday, April 10th, 2021.

During one performance, Kid Cudi, stepped out wearing a maxi-length floral dress, in a move that was deemed to be paying tribute to the late Nirvana frontman, Kurt Cobain, who passed away almost 27 years ago to the day.

"Kid Cudi is serving in this floral dress! I know that's right," wrote one Twitter user, while another added, "It’s on sight if I see people mocking Kid Cudi for wearing a dress."

4. Vin Diesel

The Fast and Furious star preempted Kanye by wearing a leather kilt to an awards ceremony in Scotland back in 2003. Vin Diesel wore a folded leather kilt with a black jumper and some matching leather boots.

Whether it was a nod to Scotland's customs and traditions, or entirely his fashion sense, I think we can all agree that the action star looked great wearing a kilt.

size-full wp-image-1263111068
(Credit: Alamy)

5. Jared Leto

Jared Leto has donned dresses and skirts on a number of occasions, and he's proud of the fact. The actor and 30 Seconds to Mars singer once took to Twitter to assert, "Real Men Wear Skits," and we completely agree.

Most notably, Leto wore a silk, red high-neck gown by Gucci at the camp-themed Met Gala back in 2019. He completed the look with shoulder pads, a jewel-encrusted body chain, and his own head — which he carried as an accessory, as a homage to one very iconic Gucci runway.

size-full wp-image-1263111092
(Credit: Alamy)

6. Post Malone

Post Malone channelled rock legend, Kurt Cobain, when he wore a dress to pay tribute to the late Nirvana frontman in April of 2020.

The rapper put on a concert to raise funds for the WHO’s COVID-10 Solidarity Response Fund, and he recreated the iconic look Cobain wore to a 1990 concert in Amherst, Massachusetts. Clad in a long floral dress, Malone also covered classics like Heart Shaped Box and Lithium.

You can watch the live stream, and check out Post's homage to Cobain below.

7. Gerard Butler

Gerard Butler has paid tribute to his native Scotland by wearing a kilt on several occasions.

That didn't stop him from having a wardrobe disaster, however. The actor revealed that he once inadvertently flashed the congregation while attending his sister's wedding.

"I had to do the first reading, so I was on the alter — it was a Catholic wedding, it was like 400 people in the congregation [...] I look down... and my kilt is spread wide... facing the whole congregation. So I slowly like cross my legs," he hilariously disclosed.

size-full wp-image-1263111098
(Credit: Alamy)

8. Billy Porter

Billy Porter doesn't shy away from wearing dresses on the red carpet – and he just dazzles in them.

The Pose actor pushed boundaries by wearing a Christian Siriano ballgown to the 2019 Oscars. Reflecting on the iconic look to Vogue, he said: "My goal is to be a walking piece of political art every time I show up. To challenge expectations.

"What is masculinity? What does that mean? Women show up every day in pants, but the minute a man wears a dress, the seas part," he continued. "It happened to me at the Golden Globes [when I wore a pink cape], and I was like, really? Y’all trippin’? I stopped traffic! That Globes outfit changed everything for me. I had the courage to push the status quo. I believe men on the red carpet would love to play more."

size-full wp-image-1263111103
(Credit: Alamy)

9. Jaden Smith

Jaden Smith is known for dressing in a gender-fluid style, and even became the face of Louis Vuitton's womenswear back in 2016. The then 17-year-old told Nylon that he wanted his style to change the way that young, Black men viewed fashion.

"So, you know, in five years when a kid goes to school wearing a skirt, he won’t get beat up and kids won’t get mad at him," he said. "It was lit because we all knew that we were going to impact the culture and change the game and make a difference."

 "If I Wanna Wear A Dress, Then I Will, And That Will Set The New Wave..." Smith tweeted in 2018.

10. Jonathan Van Ness

Queer Eye star, Jonathan Van Ness, has worn an array of dresses over the years, and he isn't afraid to clap back at trolls who criticise him for doing so.

Replying to a negative Instagram comment after he wore a dress to the 2019 Emmys, he said, "I look f*cking stunning and my name is Jonathan, snap chat filter using on your insta tiny circle private profile having self [sic]."

"The guy in the dress' is insulting and for anyone that doesn't see the implications is blind. People I'm too tired [sic]," he added.

size-full wp-image-1263111125
(Credit: Alamy)

10 times male celebrities have worn skirts or dresses – and absolutely nailed it

vt-author-image

By VT

Article saved!Article saved!

We all know that Madonna isn't afraid to break boundaries when it comes to fashion, and neither is her 15-year-old son, David Banda.

The teenager proved that gender norms are a thing of the past as he donned a long cream dress in an Instagram video his mother shared online on Sunday. "Confidence is Everything," she captioned the clip.

But David isn't the only one — in fact, there's a slew of male celebrities who are super confident when it comes to rocking dresses and skirts.. Here's just 10 of them...

size-full wp-image-1263111134
(Credit: Instagram / Madonna)

1. Harry Styles

Harry Styles broke the internet earlier in November of 2020 after appearing on the cover of Vogue. The former One Direction star is not only the first solo male to appear on the prestigious magazine's cover, but he did so while donning a dress.

Speaking about his decision to depart from conventional gender norms, he told the publication: "Clothes are there to have fun with and experiment with and play with."

"What’s really exciting is that all of these lines are just kind of crumbling away," he added. "There’s so much joy to be had in playing with clothes. I’ve never really thought too much about what it means — it just becomes this extended part of creating something."

2. David Beckham

David Beckham once wore a sarong with fashionista wife, Victoria Beckham, while the pair was vacationing back in 1998.

While the Daily Mail reports that the former professional football player attracted criticism at the time, Beckham later told ITV's Lorraine that he doesn't regret his sartorial choice.

"Sarongs are great. That's one thing I never regret because I thought it looked great and I would still wear it now," he said. "Over the years it's not just myself, everybody looks back at old pictures of themselves and thinks, 'I can't believe I wore that, or I wish I hadn't worn that, or what was I thinking?'"

3. Kanye West

Back in 2011, Kanye wore a Givenchy leather kilt on his Watch the Throne tour. Writing about the divisive item of clothing four years later, in PAPER, he said that the stye move actually solidified his reputation as a trendsetter.

"I paid my dues when I had to wear a kilt in Chicago, and friends would say, 'What's your boy got on?'," he explained. "There are warriors that have killed people in kilts in the past. Who gets to decide what's hard and what's not hard?"

Well said, Kanye.

4. Kid Cudi

Kid Cudi was praised online after performing on Saturday Night Live while wearing a floral dress on Saturday, April 10th, 2021.

During one performance, Kid Cudi, stepped out wearing a maxi-length floral dress, in a move that was deemed to be paying tribute to the late Nirvana frontman, Kurt Cobain, who passed away almost 27 years ago to the day.

"Kid Cudi is serving in this floral dress! I know that's right," wrote one Twitter user, while another added, "It’s on sight if I see people mocking Kid Cudi for wearing a dress."

4. Vin Diesel

The Fast and Furious star preempted Kanye by wearing a leather kilt to an awards ceremony in Scotland back in 2003. Vin Diesel wore a folded leather kilt with a black jumper and some matching leather boots.

Whether it was a nod to Scotland's customs and traditions, or entirely his fashion sense, I think we can all agree that the action star looked great wearing a kilt.

size-full wp-image-1263111068
(Credit: Alamy)

5. Jared Leto

Jared Leto has donned dresses and skirts on a number of occasions, and he's proud of the fact. The actor and 30 Seconds to Mars singer once took to Twitter to assert, "Real Men Wear Skits," and we completely agree.

Most notably, Leto wore a silk, red high-neck gown by Gucci at the camp-themed Met Gala back in 2019. He completed the look with shoulder pads, a jewel-encrusted body chain, and his own head — which he carried as an accessory, as a homage to one very iconic Gucci runway.

size-full wp-image-1263111092
(Credit: Alamy)

6. Post Malone

Post Malone channelled rock legend, Kurt Cobain, when he wore a dress to pay tribute to the late Nirvana frontman in April of 2020.

The rapper put on a concert to raise funds for the WHO’s COVID-10 Solidarity Response Fund, and he recreated the iconic look Cobain wore to a 1990 concert in Amherst, Massachusetts. Clad in a long floral dress, Malone also covered classics like Heart Shaped Box and Lithium.

You can watch the live stream, and check out Post's homage to Cobain below.

7. Gerard Butler

Gerard Butler has paid tribute to his native Scotland by wearing a kilt on several occasions.

That didn't stop him from having a wardrobe disaster, however. The actor revealed that he once inadvertently flashed the congregation while attending his sister's wedding.

"I had to do the first reading, so I was on the alter — it was a Catholic wedding, it was like 400 people in the congregation [...] I look down... and my kilt is spread wide... facing the whole congregation. So I slowly like cross my legs," he hilariously disclosed.

size-full wp-image-1263111098
(Credit: Alamy)

8. Billy Porter

Billy Porter doesn't shy away from wearing dresses on the red carpet – and he just dazzles in them.

The Pose actor pushed boundaries by wearing a Christian Siriano ballgown to the 2019 Oscars. Reflecting on the iconic look to Vogue, he said: "My goal is to be a walking piece of political art every time I show up. To challenge expectations.

"What is masculinity? What does that mean? Women show up every day in pants, but the minute a man wears a dress, the seas part," he continued. "It happened to me at the Golden Globes [when I wore a pink cape], and I was like, really? Y’all trippin’? I stopped traffic! That Globes outfit changed everything for me. I had the courage to push the status quo. I believe men on the red carpet would love to play more."

size-full wp-image-1263111103
(Credit: Alamy)

9. Jaden Smith

Jaden Smith is known for dressing in a gender-fluid style, and even became the face of Louis Vuitton's womenswear back in 2016. The then 17-year-old told Nylon that he wanted his style to change the way that young, Black men viewed fashion.

"So, you know, in five years when a kid goes to school wearing a skirt, he won’t get beat up and kids won’t get mad at him," he said. "It was lit because we all knew that we were going to impact the culture and change the game and make a difference."

 "If I Wanna Wear A Dress, Then I Will, And That Will Set The New Wave..." Smith tweeted in 2018.

10. Jonathan Van Ness

Queer Eye star, Jonathan Van Ness, has worn an array of dresses over the years, and he isn't afraid to clap back at trolls who criticise him for doing so.

Replying to a negative Instagram comment after he wore a dress to the 2019 Emmys, he said, "I look f*cking stunning and my name is Jonathan, snap chat filter using on your insta tiny circle private profile having self [sic]."

"The guy in the dress' is insulting and for anyone that doesn't see the implications is blind. People I'm too tired [sic]," he added.

size-full wp-image-1263111125
(Credit: Alamy)