Female celebrities from Nicki Minaj to Jennifer Lopez, often push the fashion envelope with their daring red carpet ensembles, catching the world’s attention by showing up in top designer dresses that show enough skin to make people wonder if anything is going to pop out. Then you have those that go the opposite route, and decide to have a variation on a suit or other traditionally “male” look, adding a touch of flair to otherwise routine proceedings. The one thing that they all have in common: no matter how daring, these female celebs always manage to look completely stunning.
But what about male celebrities? Why should they be left to tuxes and suits? Why aren’t they allowed to stun the world by rocking their own version of a dress or skirt, pushing the envelope as far as it can go. Well, many have, and while it is not a recent trend that popped up out of nowhere, donning a dress or skirt (sometimes in the form of a kilt) is on the rise. Though some did not always get the best reaction, their courage and I-don’t-give-a-you-know-what attitude really helped pull off the look. As the old saying goes: if you got the legs to flaunt what you were given, might as well show them off.
10. Jaden Smith
Jaden Smith, son of Will Smith and Jada Pinkett-Smith, made quite a splash when he wore a black sweater dress layered under a white tank top on Coachella Eve. He also accessorized with a pouch pendant necklace, a leather backpack, and leopard-print tube socks. Though the younger Smith tends to be very fashion forward, most of the world was taken by surprise. However, true fans of The Karate Kid star already knew that Smith was going to shake things up when he posted a photo of himself on Instagram with the following statement: “’Went to TopShop to Buy Some Girl Clothes, I Mean ‘Clothes.’” He later went on to tweet: “That Moment When Your Wearing A Dress With No Pants And You Swerve Way To Hard.” Maybe with a bit more practice, he can get the hang of it.
9. Jared Leto
A recent poster boy for outrageous fashion (not to mention helping make the term “manbun” a common phrase), Jared Leto certainly knows how to get people’s attention when it comes to the clothes he wears out on the red carpet. In 2014, the Dallas Buyers Club star took his apparel to new heights when he showed up to the 2014 iHeartRadio Music Awards in a black skirt over some trousers that was paired with a printed shirt and light blue jacket. Some could argue that the former My So-Called Life heartthrob was rocking a kilt instead, but no one can deny that it was still quite a bold choice.
8. 2 Chainz
With stars such as Nicki Minaj, Amber Rose and Brandy attending the 2013 BET Music Awards, one would think that their outfits would be the ones that all the people were talking about. They might have been at first, that is until rapper 2 Chainz showed up on the red carpet in a black sweater dress, which he accessorized with gold bling. The Birthday Song singer later changed into a leather pants outfit complete with fringe, however his bold opening ensemble surely had jaws dropping.
7. Vin Diesel
On first glance people might have mistaken Vin Diesel’s choice of attire as a skirt when he co-hosted the MTV Europe Music Awards in 2003. However, the Fast and Furious star was actually dressed in a black leather kilt. Diesel also completed the look with a black sweater and heavy black boots, adding to the warrior feel of his outfit. This was a fitting choice, considering that the awards ceremony took place in Edinburgh, Scotland. As if getting a glimpse of the Riddick star’s legs weren’t enough, Diesel also delighted fans when he took to the stage and sang Flower of Scotland.
6. Marc Jacobs
Legendary fashion designer, Marc Jacobs is known for his taste in clothes, which is probably why he has over 200 retail stores in about 80 countries. That taste also includes taking risks with his own wardrobe, which was channeled through skirts in 2008, when Jacobs showed up at one of his shows wearing his take on the kilt. The designer liked them so much, since they felt so comfortable, he even decided to wear one to jury duty. However, Jacobs later got tired of them and decided to stick to Prada pencil skirts. Hey, if you got the legs for them, why the heck not.
5. David Bowie
Singer David Bowie has had a long varied career. Not only has he belted out memorable tunes like Life on Mars, Bowie has also dabbled into acting, with crazy memorable roles in movies like Labyrinth. Of course, when you have been around as long as Bowie has, your look was bound to change over the years. During his early career, most notably his Ziggy Stardust days, rocker David Bowie took on an androgynous persona that took the world by storm. Of his many fashion risks, Bowie was known to put on a dress or two.
4. Steven Tyler
No one can deny that Steven Tyler has a look all of his own; a combination of cool rocker and Jack Sparrow, Tyler knows how to work whatever he wears. That was also the case when he decided to surprise the new American Idol judges in 2013, by showing up for the auditions in drag. Rocking what could only accurately be called a snake-skin miniskirt that was paired with black leggings, heels and a blonde wig, the Dude Looks Like a Lady singer channeled his inner diva and sang his heart out, all while making the new (but later replaced) judges laugh uncontrollably.
3. Dennis Rodman
Dennis Rodman was always a colorful character, both on and off the basketball court. The same could also be said of the bad boy of basketball’s style, which he was never shy about flaunting; feather boa’s, make-up, leather, they were all completely fair game, and Dennis Rodman wore them proudly. But for an August 1996 signing of his memoir Bad as I Wanna Be, the former Chicago Bulls player decided to take the ultimate fashion risk when he showed up in a wedding dress, complete with white gloves, blonde wig and a veil.
2. Adam Lambert
American Idol runner-up Adam Lambert has never been shy about taking his fashion to the next level, showboating around in pure glam-rock glory. So it probably would not surprise anyone to find out that the If I Had You singer was walking around in a kilt during a stop on one of his world tours. Of course, we can all agree that if anyone on this list could pull off the look, it has to be Adam Lambert.
1. Trey Parker and Matt Stone
Naturally, the creators of an outrageous show such as South Park pushed the envelope any chance they got, and that was certainly the case when Trey Parker and Matt Stone showed up to the 2000 Academy Awards in their take on two of the most iconic dresses in Academy Awards history. For his look, Stone decided to mimic Gwyneth Paltrow’s pink dress, while Parker donned Jennifer Lopez’s notorious green dress with the plunging neckline. Okay, so they admittedly may not have been in the “right” frame of mind when they did it, but kudos for the duo for trying their best to not bring attention to the fact that they were wearing dresses.
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